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大学英语指南英文A Guide to University EnglishUniversity is an exciting time, and one of the most significant challenges many students face is adapting to the language demands of higher education. Whether you are a native English speaker or learning English as a second language, the academic style and vocabulary required in university classes and assignments can be vastly different from what you are used to. However, with the right preparation and strategies, you can succeed in mastering university-level English.One of the key differences between high school and university-level English is the emphasis on critical thinking and analysis. In high school, the focus is often on recalling and summarizing information. At the university level, instructors expect you to delve deeper, to evaluate arguments, to consider multiple perspectives, and to develop your own well-reasoned opinions. This shift can be daunting, but it is essential for success in your studies.To develop your critical thinking skills, it is important to engage actively with the course materials. Do not simply read or listen passively - instead, ask questions, challenge assumptions, and look for connections between different ideas and concepts. Take notes that go beyond just listing facts and instead capture your own thoughts and reflections. When writing essays or research papers, make sure to present a clear thesis statement and support it with evidence from reliable sources.In addition to critical thinking, university-level English also requires a more formal and academic writing style. Gone are the days of casual, conversational language. Instead, you will need to master the conventions of academic writing, which include using appropriate tone, avoiding contractions and slang, and citing sources correctly. Pay close attention to the formatting and citation style specified by your instructor, whether it is APA, MLA, or another style.One of the most important aspects of academic writing is the ability to synthesize information from multiple sources. Rather than relying on a single textbook or website, you will be expected to consult a variety of scholarly sources, such as journal articles, books, and credible online resources. Carefully evaluate the reliability and relevance of these sources, and then integrate the information into your own original analysis and arguments.Vocabulary is another crucial component of university-level English. The language used in academic texts and class discussions can be highly specialized and technical, covering a wide range of disciplines from the sciences to the humanities. To keep up, you will need to expand your vocabulary and develop strategies for understanding unfamiliar terms. This might involve using context clues, consulting dictionaries or glossaries, or even studying word roots and prefixes.Effective note-taking is also essential for success in university English. Whether you are attending a lecture, participating in a seminar, or reading a textbook, you will need to capture the key ideas and information in a concise and organized manner. Experiment with different note-taking methods, such as outlining, mind mapping, or the Cornell method, to find the approach that works best for you.Finally, do not underestimate the importance of active class participation. University instructors often use discussion-based formats, and they expect students to engage actively with the material and with each other. This can be challenging for some students, particularly those who are more introverted or who are learning English as a second language. However, participating in class discussions not only helps you better understand the course content but also demonstrates to your instructor that you are actively engaged and invested in your learning.In conclusion, navigating the language demands of university-level English can be a significant challenge, but with the right strategies and mindset, you can succeed. By developing critical thinking skills, mastering academic writing conventions, expanding your vocabulary, honing your note-taking abilities, and actively participating in class, you can become a confident and effective communicator in the university setting. Remember, the journey may be challenging, but the rewards of mastering university-level English will serve you well throughout your academic and professional career.。
心得体会三个更加注重心得体会英文回答:Three Cs to Enhance Reflection:1. Clarity: Ensure your insights and observations are well-articulated and expressed with precision. Avoid ambiguous or imprecise language. Example: Instead of saying "The experience taught me a lot," write "The project taught me the importance of meticulous planning and effective communication."2. Connection: Demonstrate how your experiences and reflections relate to broader concepts, theories, or real-world contexts. Example: After attending a seminar on leadership, write "The principles discussed resonated with my experiences as a team manager, confirming the importance of fostering collaboration and empowering others."3. Contribution: Highlight the value and significanceof your insights. Explain how your reflections can contribute to personal growth, professional development, or the advancement of knowledge. Example: After completing a research project, write "My findings not only deepen my understanding of the topic but also have potential implications for industry practices."中文回答:更加注重心得体会的三大原则。
John Benjamins Publishing CompanyThis is a contribution from Target 22:1© 2010. John Benjamins Publishing CompanyThis electronic file may not be altered in any way.The author(s) of this article is/are permitted to use this PDF file to generate printed copies to be used by way of offprints, for their personal use only.Permission is granted by the publishers to post this file on a closed server which is accessible to members (students and staff) only of the author’s/s’ institute, it is not permitted to post this PDF on the open internet.For any other use of this material prior written permission should be obtained from the publishers or through the Copyright Clearance Center (for USA: ). Please contact rights@benjamins.nl or consult our website: Tables of Contents, abstracts and guidelines are available at ObituaryProf. Dr. Dr. h.c. Hans J. VermeerHeidemarie SalevskyBerlin“cuncta fluunt, omnisque vagans formatur imago; ipsa quoque adsiduo labunturtempora motu, non secus ac flumen; neque enim consistere flumen nec levis horapotest: sed ut unda inpellitur unda urgeturque prior veniente urgetque priorem,tempora sic fugiunt pariter pariterque sequuntur et nova sunt semper; nam quodfuit ante, relictum est, fitque, quod haut fuerat, momentaque cuncta novantur.”(Ovid : Metamorphoses, Book XV: 177–185)The community of translation scholars has lost one of its most distinguished members. On February 4, 2010, Prof. Dr. Dr. h.c. Hans Josef Vermeer died in Hei-delberg, Germany. He would have turned eighty on September 24 of this year. His family placed the following words above the announcement of his death: “When an old man dies a library burns.” I would like to modify this statement somewhat: “When a scholar of Hans Vermeer’s calibre dies a library burns.”Hans Vermeer was a very special kind of person. Right until the final weeks of his life he devoted his energies to his chosen field, Translation Studies. He did pio-neering work in shedding light on translating and interpreting. The announcement of his death posted by his colleagues, friends and pupils (Süddeutsche Zeitung, Feb-ruary 13, 2010) lists 41 names, including such well-known professors of our disci-pline as Rosemary Arrojo, Justa Holz-Mänttäri, Mary Snell-Hornby, Klaus Kaindl, Gauti Kristmansson, Franz Pöchhacker, Erich Prunč, Katharina Reiß, Miriam Sh-lesinger, Gideon Toury and Lawrence Venuti to mention just a few.Hans Vermeer was a translation scholar who had the ability to navigate the paradigm shifts in theory, to follow the numerous different threads in history and to demonstrate how these run in parallel, cross each other, gradually intertwine or interconnect. He was at ease in adjacent disciplines such as philosophy or rhetoric, and au fait with translators’ comments on their work in the past and present, as well as with developments in literary history and Bible translations. Hans Ver-meer was equally at home with the absolutization of the idea in Plato, the un-successful imitatio concept of the Renaissance, the culturally sensitive approaches2Heidemarie Salevskyof Wilhelm von Humboldt and Friedrich Daniel Ernst Schleiermacher and the relapse into reductionism associated with the ostensibly rigorous scholarship of the 19th-century.In his quest for the roots — always using the relevant languages — Hans Ver-meer gained insights for the present era, identified fundamental positions as ex-planations and conditions for resulting attitudes in theory and practice, engaged in source criticism, pointed out explicit and implicit theoretical approaches and provided impressive illustrations of the links between “external” and “internal”translation history. Hans Vermeer embedded theoretical approaches in the course of translation history, unearthing examples to support the skopos theory which he established. Even so, he never failed to point out, to quote Hamlet’s words “there is nothing either good or bad, but thinking makes it so”, that no theory is unrelated to space, time and situation. This was very helpful, not least in the East-West debate after German reunification, when Hans Vermeer in 1992 accepted my invitation toa visiting professorship at the Department of Translation Studies of Humboldt Uni-versity in Berlin (Institute of Slavonic Studies) which I directed at the time. Before that I had served as a visiting professor at the Ruprecht Karls University in Hei-delberg in 1991. Hans Vermeer had attended my lectures in Heidelberg and I had attended his in Berlin, both periods being marked by intensive discussions, and not just about subject-specific matters. We had first met at an international meet-ing held in the GDR in September 1989, i.e. a few weeks before the fall of the Wall.A prominent characteristic of Hans Vermeer was his openness, which alwaysproved an asset during discussions at the Research Seminar on Translation Stud-ies. When this discussion forum was established at Berlin’s Humboldt University in March 1989, it never occurred to me that the first event would be followed by another seventy six and that over the following twenty years Hans Vermeer would put on seven events either alone or together with others. I vividly remember the event in 1992 devoted to the translation of the Decalogue at the Theological Fac-ulty of Humboldt University and also the interdisciplinary colloquium to mark the 225th anniversary of the birth of the German theologian, philosopher and philolo-gist Friedrich Daniel Ernst Schleiermacher in November 1993. Hans Vermeer also read a paper dealing with language and culture at the international conference held in 1995 to mark 100 years of training translators and interpreters for Russian at Berlin University (1894–1994).After my place of work had changed to Magdeburg in 1996 we had very ani-mated discussions there in 1998 about the need to change the curriculum. In 2004, at the seventieth event marking fifteen years of the Research Seminar, our discus-sions about his paper on the enhancement of translation and reflections on Jacques Derrida were just as animated. Small wonder, then, that the Research Seminar organized an honorary colloquium to mark Hans Vermeer’s seventy fifth birthdayProf. Dr. Dr. h.c. Hans J. Vermeer 3 in 2005. It was met with a lively response, attracting scholars from Austria, Brazil, Britain, Finland, Turkey, the United States and several German universities.Hans Vermeer opened doors — between disciplines and between universities, for example at the conference on problems with translator and interpreter training curriculums in the former East and West Germany in November 1991, that is ata time when he held the chair of Translating and Interpreting Studies and Portu-guese at the Ruprecht Karls University in Heidelberg.Hans Vermeer always allowed us to share his scholarly curiosity and the plea-sure he derived from research. His publications, his lectures in Berlin and the pa-pers presented at the Research Seminar always took us on journeys of adventure across the centuries, sometimes involving excursions into intriguing and occa-sionally amusing thematic sideshows, and they were always manifestations of a brilliant mind of breathtaking erudition. They drew our attention to what might be and provided an opportunity to measure out the space that opened up and revealed a light that made something else visible, namely perspectives. The result was changes both in our discipline and in the way people felt and thought aboutits problems.For all those who admired Hans Vermeer not “only” as a scholar, but also asa friend, it was a great joy to see that decades of work devoted to teaching and research ultimately earned him the highest accolade a scholar can hope to receive. On January 17, 2010 the University of Mainz/Germersheim conferred an honor-ary doctorate on Hans Vermeer. This was the first to be granted in Translation Studies at any German university.At the University of Mainz in Germersheim Hans Vermeer was Professor of General and Applied Linguistics from 1971 to 1983 before he was offered the chairof Translation Studies with special reference to Portuguese at Heidelberg Univer-sity in 1984, which he held until becoming an emeritus professor in 1992. After spells as a visiting professor at Leopold Franzens University in Innsbruck/Austria from 1999 to 2002, at Boğaziçi University (Bosphorus University) in Istanbul from 2002 to 2003 and finally at Okan University in Istanbul from 2004 till the winter semester of 2007/08, Hans Vermeer returned to the University of Heidelberg andto the University of Mainz in Germany to teach in the final years of his life.The honorary doctorate was a well-deserved tribute to a scholar with over 300 publications to his credit in which he continually reappraised and questioned what he (and others) had said, displaying a stunning knowledge of literature.Hans Vermeer’s first publication can be traced back to the year 1959 and con-cerned the Portuguese language. Contributions to German studies were made from 1960 onwards, and in 1963 he began to publish works dealing with linguis-tics and indology. This was also the period when he turned to translation studies and foreign language teaching for the first time.4Heidemarie SalevskyHis editing career began in 1986 with the periodical TEXTconTEXT. The series translatorisches handeln followed in 1989 and the series TEXTconTEXT Wissen-schaft somewhat later.There is no need to mention the standard works because they are well known.But who could have written the seven volumes on the history of translation and translation theory other than someone who was as familiar with Hebrew, Greek and Latin as with various Romance languages and English, someone who was both an Indologist and well versed in the historical development of the German lan-guage.One of Hans Vermeer’s books that left a particularly deep impression on me was Skizzen zu einer Geschichte der Translation. It always seemed to me that Hans Vermeer himself lived up to the quotation (after Anguttara Nikaya 3,66) which precedes the second part of the first volume of this work:Geht nicht nach Hörensagen, Überlieferungen, Tagesmeinungen, Autorität hei-liger Schriften, Vernunftsgründen, logischen Schlüssen, Theorien, Meinungen,persönlichen Vorlieben und Autorität! Wenn ihr selber erkennt, dass etwas un-gut, verwerflich und tadelnswert ist und zu Unheil führt, dann gebt es auf. Wennihr selber erkennt, dass etwas gut, untadelig und lobenswert ist und zu Segen undHeil führt, dann macht es euch zu eigen. (Nach dem Anguttara Nikaya 3,66)1 Vermeer’s last article “Vom Altern der Texte” will be published posthumously in Berlin.Heidemarie SalevskyThe Board of Target wants to join the many colleagues mentioned by Heidemarie Salevsky in their expression of respect for the memory of Professor Hans Vermeer.They consider his work as a truly monumental contribution to the development of Translation Studies during recent decades. Several of us particularly remember Pro-fessor Vermeer as a most inspiring CERA Chair Professor at K.U. Leuven in 1990.List of books on Translation Studies1983 Aufsätze zur Translationstheorie; Heidelberg.1984 (with Katharina Reiß) Grundlegung einer allgemeinen Translationstheorie; Tübingen (= Linguistische Arbeiten 147) — 21991. — Finnish translation by Pauli Roinila: Mitä kään-täminen on. Teoriaa ja käytäntöa; (Helsinki 1986). — Spanish translation by Sandra Gar-cía Reina and Celia Martín de León with Heidrun Witte as consultant and coordinator:Fundamentos para una teoría funcional de la traducción; (Madrid 1996).1986 voraus-setzungen für eine translationstheorie — einige kapitel kultur- und sprachtheorie.Heidelberg.Prof. Dr. Dr. h.c. Hans J. Vermeer 5 1992 Skizzen zu einer Geschichte der Translation, Bd. 1 und 2; (Frankfurt a. M.) (= thw 6.1f). 1996 A skopos theory of translation (Some arguments for and against); Heidelberg (= TEXTcon-TEXT Wissenschaft 1)Die Welt, in der wir übersetzen. Drei translatologische Überlegungen zu Realität, Vergleichund Prozeß; Heidelberg (= TEXTconTEXT Wissenschaft 2).Übersetzen als Utopie — Die Übersetzungstheorie des Walter Bendix Schoenflies Benjamin;Heidelberg (= TEXTconTEXT Wissenschaft 4).Das Übersetzen im Mittelalter (13. und 14. Jahrhundert), Bd. 1: Das arabisch-lateinischeMittelalter — Bd. 2: Deutsch als Zielsprache — Bd. 3: Literaturverzeichnis und Register;Heidelberg (= TEXTconTEXT 4.1–3).2000 Das Übersetzen in Renaissance und Humanismus (15. und 16. Jahrhundert) — Band 1: Westeuropa; Band 2: Der deutschsprachige Raum, Literatur und Indices; Heidelberg:TEXTconTEXT (= TEXTconTEXT Wissenschaft 6f).2006 Luhmann’s “Social Systems” Theory: Preliminary Fragments for a Theory of Translation;Berlin: Frank & Timme.Versuch einer Intertheorie der Translation; Berlin: Frank & Timme.2007 Ausgewählte Vorträge zur Translation und anderen Themen — Selected Papers on Transla-tion and other Subjects; Berlin: Frank & Timme (= TransÜD 13).Note1. The Standard English translation (from the Pali, by Ñanamoli Thera) of the fragment of the Salha Suttra on which Vermeer draws here reads as follows (see /accesstoinsight/html/tipitaka/an/an03/an03.066.than.html:… do not be satisfied with hearsay or with tradition or with legendary lore or with what has come down in scriptures or with conjecture or with logical inference or with weighing evidence or with a liking for a view after pondering it or with someone else’s ability or with the thought ‘The monk is our teacher.’ When you know in yourself ‘These things are unprof-itable, liable to censure, condemned by the wise, being adopted and put into effect, they lead to harm and suffering,’ then you should abandon them.…W hen you know in yourself: ‘These things are profitable, blameless, commended by the wise, being adopted and put into effect they lead to welfare and happiness,’ then you should practice them and abide in them…Author’s addressProfessor Dr. Heidemarie SalevskyFachbereich Kommunikation und MedienHochschule Magdeburg-Stendal (FH)Breitscheidstr. 2, Haus 1, Raum 1.12D-39114 MAGDEBURGGermanyheidemarie.salevsky@hs-magdeburg.de。
Mirror stageLacan's first official contribution to psychoanalysis was the mirror stage, which he described as "formative of the function of the I as revealed in psychoanalytic experience." By the early 1950s, he came to regard the mirror stage as more than a moment in the life of the infant; instead, it formed part of the permanent structure of subjectivity. In "the Imaginary order," their own image permanently catches and captivates the subject. Lacan explains that "the mirror stage is a phenomenon to which I assign a twofold value. In the first place, it has historical value as it marks a decisive turning-point in the mental development of the child. In the second place, it typifies an essential libidinal relationship with the body-image".[35]As this concept developed further, the stress fell less on its historical value and more on its structural value.[36] In his fourth Seminar, "La relation d'objet," Lacan states that "the mirror stage is far from a mere phenomenon which occurs in the development of the child. It illustrates the conflictual nature of the dual relationship."The mirror stage describes the formation of the Ego via the process of objectification, the Ego being the result of a conflict between one's perceived visual appearance and one's emotional experience. This identification is what Lacan called alienation. At six months, the baby still lacks physical co-ordination. The child is able to recognize themselves in a mirror prior to the attainment of control over their bodily movements. The child sees their image as a whole and the synthesis of this image produces a sense of contrast with the lack of co-ordination of the body, which is perceived as a fragmented body. The child experiences this contrast initially as a rivalry with their image, because the wholeness of the image threatens the child with fragmentation—thus the mirror stage gives rise to an aggressive tension between the subject and the image. To resolve this aggressive tension, the child identifies with the image: this primary identification with the counterpart forms the Ego.[36] Lacan understands this moment of identification as a moment of jubilation, since it leads to an imaginary sense of mastery; yet when the child compares their own precarious sense of mastery with the omnipotence of the mother, a depressive reaction may accompany the jubilation.[37]Lacan calls the specular image "orthopaedic," since it leads the child to anticipate the overcoming of its "real specific prematurity of birth." The vision of the body as integrated and contained, in opposition to the child's actual experience of motor incapacity and the sense of his or her body as fragmented, induces a movement from "insufficiency to anticipation."[38] In other words, the mirror image initiates and then aids, like a crutch, the process of the formation of an integrated sense of self.In the mirror stage a "misunderstanding" (méconnaissance) constitutes the Ego—the "me" (moi) becomes alienated from itself through the introduction of an imaginary dimension to the subject. The mirror stage also has a significant symbolic dimension, due to the presence of the figure of the adult who carries the infant. Having jubilantly assumed the image as their own, the child turns their head towards this adult, who represents the big Other, as if to call on the adult to ratify this image.[39]35. Lacan, J., "Some Reflections on the Ego" in Écrits36.Dylan Evans, An Introductory Dictionary of Lacanian Psychoanalysiscan, J., "La relation d'objet" in Écrits.can, J., "The Mirror Stage as Formative of the Function of the I", in Écrits: a selection, London, Routledge Classics, 2001; p. 5can, Tenth Seminar, "L'angoisse," 1962–1963。
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【副题名】从拉康的镜像阶段理论解读《了不起的盖茨比》【摘要】美国小说家司各特·菲茨杰拉德深深抓住了时代的主旋律,其中篇小说《了不起的盖茨比》生动形象地折射出美国现代化过程中个体的感受,向我们生动呈现了二十世纪二十年代处于转型时期美国社会的全景画面。
那个时代以追求喧嚣、名利、金钱为主流,放荡的性行为、欺诈等不道德行为成为“喧嚣时代”的代名词,作者也因其生动记录了浮华世象掩盖下人们生活的腐化、堕落以及精神的严重空虚,而被誉为“爵士乐时代”的代言人。
《了不起的盖茨比》因思想深度和艺术表现力而成为美国文学的典范,也因其叙事手段的多样性、文本的多义性及其深刻的历史记录享誉世界文坛。
二十世纪八十年代以来,随着各种文学理论的涌现,对《了不起的盖茨比》的研究摆脱了以往从作者生平解读文本的传统窠臼,许多专家、学者重新从新的理论视角去解读。
其中有运用女性主义观点批判小说中女性生存状况,有运用社会文化角度探讨消费主义;还有从解构主义、后殖民主义等视角去解读文本。
总而言之,对这部小书的解读主要集中在对美国梦的独特阐释、别具一格的叙事技巧和文体风格等方面,但很少有批评家和文论者从拉康的镜像阶段理论去解读《了不起的盖茨比》。
拉康的镜像理论主要是从后解构主义发展而来的心理学说,它主要关于自我的建构、自我身份的确立;父亲之名及其象征意义;镜像误认以及镜像认可的一种理论。
论文以拉康的镜像阶段理论为切入点,进一步发掘盖茨比悲剧的深层原因,详细考察主人公梦想失败的自身因素,旨在提供一种新的解读途径,以便在前人研究成果的基础上,更深入地探究盖茨比悲剧的必然性。
小说中的主人公因拒绝父亲之名的存在以及镜像混淆及误认,从而一直生活在现实和镜像之间的混乱状态之中,最终导致无根的状态和自我的迷失。
论文主要分五个部分。
第一部分首先简要介绍作者生平及其文学成就,并就本论文的写作目的和理论视角进行简要说明,其次回顾了国内外对《了不起的盖茨比》的研究现状以及最新进展。
第1篇一、活动背景随着我国教育改革的深入推进,英语教育作为基础学科之一,其教学质量和效果受到了广泛关注。
为了进一步提高英语教学质量,促进教师专业成长,我校英语学科组于XX年XX月XX日开展了教研活动。
本次活动旨在加强教师之间的交流与合作,提高教学水平,为学生的英语学习提供更好的服务。
二、活动目标1. 深入探讨英语教学方法,提高课堂教学效果;2. 加强教师之间的沟通与协作,形成良好的教研氛围;3. 培养教师的教学研究能力,提升教师的专业素养;4. 促进学生英语学习兴趣,提高英语学习成绩。
三、活动内容1. 课堂观摩本次教研活动首先进行了课堂观摩,由我校英语教师进行公开课展示。
教师们展示了不同的教学风格和教学方法,如情景教学法、任务型教学法、合作学习法等。
在观摩过程中,教师们认真记录,互相学习,共同探讨如何提高课堂教学效果。
2. 专题讲座为了进一步提高教师的教学水平,我们邀请了资深英语教师进行专题讲座。
讲座内容涵盖了英语教学理论、教学方法、课堂管理等各个方面。
讲座过程中,教师们积极参与互动,分享了自己的教学经验,为今后的教学工作提供了有益的启示。
3. 教学研讨在课堂观摩和专题讲座的基础上,教师们进行了教学研讨。
针对教学中的实际问题,如如何激发学生学习兴趣、如何提高学生的英语口语表达能力、如何进行有效的课堂管理等,教师们各抒己见,共同探讨解决方案。
通过研讨,教师们对教学问题有了更深入的认识,为今后的教学工作积累了宝贵的经验。
4. 教学反思在活动最后,教师们进行了教学反思。
他们回顾了自己的教学过程,分析了教学中的优点和不足,提出了改进措施。
通过反思,教师们更加明确了今后的教学方向,为提高英语教学质量奠定了基础。
四、活动成果1. 教师的教学水平得到了提高。
通过本次教研活动,教师们掌握了更多的教学方法,提高了课堂教学效果,为学生的英语学习提供了更好的服务。
2. 教师之间的沟通与协作得到了加强。
在活动过程中,教师们相互学习、相互借鉴,形成了良好的教研氛围。
Title: My Reflections on Career AchievementAs a high school student, Ive always been intrigued by the concept of career success. Recently, I attended a seminar on Career Achievement which profoundly impacted my perspective on what it means to achieve in ones professional life. Heres my take on the experience and the insights I gained.The seminar started with an inspiring keynote speech by a successful entrepreneur who shared her journey from a humble beginning to the pinnacle of success. What struck me the most was her emphasis on the importance of passion and perseverance. She mentioned that career achievement isnt just about reaching the top of the corporate ladder or earning a high salary its about finding joy in what you do and sticking to it even when the going gets tough.During the breakout sessions, we were divided into groups and tasked with discussing our own definitions of career achievement. This exercise was eyeopening as it allowed me to hear diverse viewpoints from my peers. Some believed that achieving a worklife balance was the ultimate goal, while others felt that making a significant impact in their field was the true measure of success.What resonated with me was the idea that career achievement is subjective and personal. Its not about comparing oneself to others or adhering to societal expectations. Its about setting your own goals, working towards them diligently, and finding fulfillment in the process.Moreover, the seminar highlighted the significance of continuous learning and adaptability. In todays fastpaced world, where industries are constantly evolving, its crucial to stay updated with the latest trends and technologies. This means being open to acquiring new skills and knowledge, even if it means stepping out of your comfort zone.One of the most impactful moments was when a panel of industry experts shared their experiences with failure and how they used those setbacks as stepping stones to success. It was a humbling reminder that even the most accomplished individuals have faced challenges and that its okay to stumble. What matters is the resilience to get back up and keep moving forward.In conclusion, the seminar on career achievement has broadened my horizons and given me a more nuanced understanding of what it means to be successful in ones career. Its not just about the end goal but also about the journey, the growth, and the lessons learned along the way. As I look to the future, I am more determined than ever to pursue my passions, embrace challenges, and continuously strive for personal and professional growth.。
Reflections on Process Research#Edward J.J. GrabowskiMerck Research LaboratoriesMerck & Company, Inc.Rahway, NJ 07065 USA#Dedicated to my early Merck Mentors – Ed Tristram,Roger Tull, Pete Polack, Erwin Schoenewaldt, MikeSltezinger, Earl Chamberlin, John Chemerda, Vic Grenda,Seemon Pines and Len Weinstock – a truly formidablebunch of teachers and scientists.The achievements of an organization are the results of thecombined efforts of each individual. Vince LombardiThe kind invitation of the Editors of this Symposium Series to provide an introductory chapter affords me an excellent opportunity to reflect on what has been a thirty eight year career in Process Research – all at the Merck Research Laboratories. There have been monumental changes in organic chemistry during this time, and today the field of Process Research is being pulled in more directions than ever before. Regardless, my belief is that our principal objectives remain the same: the design of practical chemical processes to support drug development, and the discovery and definition of new synthetic methods to support process activities.When I was interviewing for a job in 1965 as the completion of my doctoral research approached, my thought was to be a medicinal chemist and engage in that alluring area called ‘basic research’. I suffered all of the preconceived notions about ‘process research’, and thought that I would have none of it. Anumber of the process groups that I visited clearly fit the stereotype, until, of course, my interview with the Process Group at Merck. Max Tishler organized the group along non-typical lines, and there was a very strong emphasis on developing new science, studying reaction mechanisms, and participating in the greater chemical community. These activities were a natural part of the group’s principal responsibility – the design and development of superb chemical syntheses and manufacturing processes to support Merck’s product pipeline. At that time the methyldopa manufacturing process, which even today stands as an outstanding example of what a good process should be, was just coming into its own.(1) The excellence and enthusiasm of the Merck Process Group was clearly evident during my interview, and I decided to make a career change before my career had begun. Thirty eight years later, I still believe that it was the right choice.During the course of my career there have been major changes in what we do and in our responsibilities, and I am not sure that I welcome all of this, nor our response to it, with enthusiasm. In addition to our major responsibilities of designing practical syntheses and manufacturing processes, and preparing bulk drug to initiate early development, we are beset with a myriad of ever-growing regulatory requirements, endless discussions about low-level impurities, when or when not to make process changes, what are process changes, compression of program timelines, increases in drug requirements to begin development, etc., etc. Over the past ten years Process Research has emerged as a recognized field in organic chemistry, with its own journal and scientific meetings. I have always maintained that process research in the pharmaceutical industry must keep a considerable overlap with the academic chemical community. We are one of the few industrial organic chemistry enterprises that has the opportunity to do basic chemical research as a normal part of our job, and we must never let go of that opportunity. This overlap with academic research keeps us in close contact with academicians, who are keenly aware that careers in process research present wonderful opportunities for their students.I would be remiss not to comment on our closest allies in R&D in a vehicle such as this, and I’d like to begin this section with some thoughts on medicinal chemists and medicinal chemistry routes to drug candidates. Clearly, the medicinal chemists are part of the most creative group in the pharmaceutical industry – the discovery effort, which I consider the most challenging and difficult endeavor in our industry. I stand in awe of their contributions, and I continually marvel at the complexity of structure and synthesis at which structure-activity studies are done. The era of methyl-ethyl-propyl is long since gone, and some of our carbapenem candidates reflect the heights to which discovery efforts aspire.(2) Such complexity in drug candidates reflects the current state of synthetic organic chemistry and organic chemists, and the armamentarium of reactions currently available. I think that process chemists often forget that the goal of medicinal chemistry is to design drug candidates,and not to design practical syntheses. Medicinal syntheses are designed for versatility, convenience and expedience. The drug candidate that results is not known when the program begins, and its initial synthesis is far from ideal by the very nature of the science. Yet process chemists persist in taking delight at setting up the medicinal synthesis of a drug candidate as a straw man to be readily pushed over with great glee. I suggest that process chemists would better serve their cause by not gloating over the inefficiencies of a first synthesis, but rather take the time to extract the best and most useful information from it and build upon it.Second amongst our co-conspirators in R&D are the chemical engineers. We all tread with fear at the first introduction of our chemistry into the pilot plant and casting it into the hands of the chemical engineers. I had once commented to Ed Paul, the head of our chemical engineering group, that the chemists felt that the first pilot plant run for a chemical process served to confirm O’Reilly’s corollary to Murphy’s Law (“Whenever something can go wrong, it will go wrong.”). O’Reilly noted that Murphy was an optimist. With a gleam in his eye, Ed responded that the engineers considered the first pilot plant run as the chemist’s final exam! In fact, there is some truth to both views, and often problems on scale-up result from an inadequate understanding of the parameters that control our chemical processes. This is more evident than ever in today’s rushed climate, where getting final drug substance as quickly as possible is often considered the major objective.Analytical chemists and pharmaceutical scientists are also our key partners. Analytical chemistry has undergone a revolution in instrumentation, but sometimes I think this creates as many problems as it solves. The pharmaceutical scientists possibly have the most complex challenges. Despite the wonderful advances in science and technology over the past decade, much of what they do still contains a strong component of art. Regardless of the plethora of data we might acquire on a final bulk form, it is still a matter of trial and error to determine a workable drug formulation. And the only test of the response of that formulation to scale-up, is the actual scale-up.One of my favorite topics in process research is chemical lore, and we have all fallen victim to it. Years ago we were designing and developing the first practicable synthesis of imipenem, the first carbapenem antibiotic to reach the market.(3) As part of this synthesis lactone 1 (Scheme 1) was solvolyzed in benzyl alcohol, which afforded a 3:1 mixture of the desired benzyl ester and the unopened lactone. This was the equilibrium ratio. The ester was cyclized to the β-lactam, which was then hydrogenolyzed to the free acid in preparation for a two-carbon chain extension. As we attempted to scale-up the benzyl alcohol solvolysis reaction, we began to recognize that such was impossible. We could not readily remove the benzyl alcohol, and as we handled the system the benzyl ester would revert to lactone. Faced with this dilemma, we wondered about solvolyzing the lactone in methanol. We were happy to note that theequilibrium ratio of the ester to lactone was now 97:3, but we were faced with the problem of hydrolyzing a methyl ester in the presence of the β-lactam. There were two parts to the established lore: everyone agreed that one could NOT successfully effect the desired hydrolysis as the β-lactam was far more reactive than the methyl ester to aqueous base; and the medicinal chemists had already demonstrated that the reaction did not work. Facing likely failure in that we could never develop the benzyl alcohol reaction into a practical process, we initially ran the hydrolysis of the methyl ester lactam with 1N NaOH in water. We were pleased that the lore was indeed wrong, and the selectivity for methyl ester hydrolysis over β-lactam opening was >100:1. Ultimately, we developed a process where the hydrolysis was done at a 30-50% concentration of the ester in water with 5N NaOH at 0°C and pH <13. The hydrolysis was exothermic and proceeded almost like a titration. After completion of the hydrolysis, the pH was adjusted to 8.5 – 9.5, and the water was evaporated at <50°C while the system was turned over to DMF in preparation for the chain extension. At 50°C and ~pH 9, the sodium salt showed no decomposition over 30 days! In fact, the t 1/2 of a 50% solution of the sodium salt at 25°C was subsequently shown to be >22 years! So my continuing advice to new process chemists is to ignore the lore of chemistry – the lore is our enemy – run the damn reaction. If it fails for the anticipated reasons, you don’t have to tell the boss! If it works, the boss will think you are a genius.3222Bn 3 Parts 232CH 2CH 397 Parts2Oo 2Na The Process:The hydrolysis is run with 5N NaOH to pH 13 at 0o The Facts:The methyl ester selectivity is >100:1t 1/2 for the Na Salt at pH 9 at 50% conc. and 25o is 22 years!Scheme 1: The lore is our enemy.Throughout my career in process research there have been a number of programs that represent, for various reasons, milestones, and I thought a recounting of some of them might be of interest to the readers of this chapter. The names of the principal contributors to these programs are listed in the references. They represent a truly excellent group of chemists, and their creativity and enthusiasm for science have been foremost in making a most enjoyable career for me. My first program at Merck was to design a new synthesis of amipramidin (2), a compound then being developed as a potassium- sparing diuretic. A very workable classical heterocyclic process for this drug was already on line in the pilot plant, and I was asked to design a synthesis beginning with 2-methylpyrazine (3) (Scheme 2). Having been trained as a synthetic organic chemist in alkaloid synthesis,(4) I must confess to a bit of dismay when I noted that not only did the target lack any stereo centers, but it had a most unspectacular proton NMR spectrum. Ready carbon spectra were still a dream at the time. Regardless, I began the program by looking at the chlorination of 2-methylpyrazine, on which there was essentially no literature. Chlorination in water at room temperature produced two moles of nitrogen trichloride, thereby starting my career with the proverbial bang! Radical chlorination readily yielded 2-trichloromethylpyrazine (4), whereas ionic chlorination followed by radical chlorination afforded 2-chloro-3-dichloromethylpyrazine (5). Treatment of 4 with excess sodium methoxide in refluxing methanol afforded a mixture of three isomeric trimethoxypyrazines, with 2-methyl-3,5,6-trimethoxypyrazine being formed in 15% isolated yield.(5) I still think this is one of the most remarkable transformations that I have ever seen, and I became an instant convert to heterocyclic chemistry. I’ll leave it to the reader to sort out the chemistry, but application of the principle behind the transformation to substrate 5 employing hydroxylamine in ethanol produced oxime 6.(6) Clearly all of the oxidation states and substitution issues to amipramidin had been resolved, and the subsequent transformations to final product were straightforward. My new synthesis did not replace the existing route, but it did initiated my career-long love affair with heterocyclic chemistry.NN N N NH 2H 2N ClN H ONH 2NH CH 3222NCl 32OH 3H 322315% Yield 6Scheme 2: Introduction to heterocyclic chemistry.During the 1970’s Merck, along with the rest of the industry, suffered from a weak candidate pipeline. We process chemists were asked to select or define an unusual scaffold amenable to simple and broad derivatization in an effort to define new lead candidates for the medicinal areas via broad pharmacological screening. Harkening back to my alkaloid days, I chose to prepare the tricyclic compound 8 based on reported chemistry from 4-cyano-N -methylpyridinium iodide (7) (Scheme 3).(7) After some failed preliminary efforts, we quickly realized that 8 was far too complex and reactive for the multitude of transformations that we wanted to employ, so we reduced the enamine double bond to form the more stable and versatile tricycle 9. Among the numerous possible reactions that we studied, we decided to heat 9 in water. A remarkable transformation ensued, wherein our substrate, which had fourteen different carbons by 13C NMR, was transformed into an isomer that showed only seven! Given that today we can do an X-ray crystal structure before lunch, this does not seem like such a difficult structural problem. However, at that time it took quite a bit of work and thought to establish 10 as the structure of the product. This remarkable rearrangement (a hydride transfer followed by ring closure of the zwitterionic intermediate) had produced a diazaditwistane with versatile functional groups just begging for further elaboration.(8) Recognizing the uniqueness of the structure we had produced, we joined with our associates in Chemical Engineering and prepared 10 kg of both 9 and 10 for derivatization work. I’ll spare the reader the odyssey of these efforts, save to note that reactionof 10 with excess benzyl Grignard furnished bis-phenylacetyl compound 11 which was 2-3 times more potent than morphine as an analgesic.(9) We began a long structure-activity study that still left us with an opiate-class analgesic. The effort taught me just how difficult medicinal chemistry really is, and I went running back to process research.N +CNCH 34N CN H 3C oN NCNCN CH 3H 3C 2653N CH 3CN N 3I -89107Scheme 3: Diazaditwistane adventures.The 1980’s brought imipenem, the world’s first carbapenem antibiotic, as the focus of our research efforts. Our goal was to define a new synthesis and ultimately process, that would supplant the one designed prior to our involvement - alluded to briefly above.(3) We began with azetidinone carboxylic acid (12), which had been previously prepared from aspartic acid in our medicinal group.(10) We were able to add the hydroxy ethyl group employing standard chemistry to afford 13 (Scheme 4). Oxidative decarboxylation with lead tetraacetate gave acetoxy azeditinone 14, and we began to believe that something important was happening. Based on a paper published by Manfred Reetz wherein 1-silyloxycyclohexene was allylated with allyl acetate in the presence of zinc bromide to afford 2-allylcyclohexanone,(11) we quickly showed that 14 reacts with a variety of silyl enol ethers to afford the corresponding ketone products under Lewis acid catalysis.(12) Remembering the diazo synthon 15 developed in the penicillin approach to imipenem,(13) we reacted compounds 14 and 15 under Lewis acid conditions to produce 16, a key intermediate in our earliest imipenem process. Clearly we had a new, and possibly one of the best, routes to imipenem. We published a preliminary communication on the work in 1982.(14) Thereafter, this route was developed to a practicable level, and combined with commercially available 14 (as the t -BDMS ether), this chemistry became one of the most direct approaches to imipenem. Our patent was ultimately granted in 1999 we now hold the rights to this process until 2016! (15)H 3H 3+ImipenemZnI 2222HH 32H H 3PNB = p -Nitrobenzyl Pb(OAc)4Scheme 4: Acetoxy azetidinone and a practical process for imipenem.In the mid-1980’s indacranone (17) came to the group, and we faced the challenge of enantiospecifically preparing a tetrasubstituted carbon center. Initially, we established the stereogenic center in intermediate 18 via an achiral phase-transfer reaction employing methyl iodide, aliquat 336, toluene and 50% sodium hydroxide. A subsequent resolution of the racemic acid provided the individual enantiomers. In thinking about how to do the same transformation enantiospecifically, we took the most simple approach initially. Rather than use the aliquat, we replaced it with simple chinchona alkaloids, thinking that these would methylate under the reaction conditions and become catalysts for chiral phase transfer chemistry. Initially our e.e.’s were less than 10%, but this provided enough encouragement that we began to make individual chinchona-derived quaternary ammonium salts. With N -benzylcinchonium chloride our e.e. reached ~30%. Simple electron-withdrawing p -substituted analogs increased the e.e., ultimately into the 60% range with the p -trifluoromethyl analog. Subsequent development resulted in the first enantioselective phase transfer alkylation process with the e.e. reaching 94%.(16, 17) This process was successfully demonstrated in the pilot plant, and supplied drug for the programuntil the demise of the candidate for toxicity reasons. We continued working on the chemistry and subsequently showed that the reaction mechanism is far more complex than anyone had envisioned, with the catalyst transferring into the organic phase as a 1:1 complex of the catalyst and its zwitterion. Subsequent deprotonation of the indanone by the catalyst dimer afforded the catalyst-substrate complex which involves two π-π stacking reactions and a hydrogen bond, all remarkably similar to the structure of the catalyst dimer. Methylation can only take place from the exposed face, yielding the observed isomer.(17)3Substrate-Catalyst Complex17Scheme 5: Chiral catalytic phase transfer alkylation chemistry.With the recent dramatic accomplishments in phase-transfer technology developed in E.J. Corey’s laboratory,(18) we have wondered about the correctness of this mechanism, since our catalyst does indeed O-methylate under our reaction conditions as an unwanted side-reaction. Could the O-methylated quaternary ammonium ion serve as the active catalyst, via a mechanism comparable to that proposed by Corey with his N-anthranceneylmethyl-O-allyl (or benzyl) analogs of the cinchona alkaloid catalysts as used in amino acid syntheses? In separate experiments, we had shown that the O-methyl catalyst does not function in our indanone case. With the reaction clearly half-order with respect to catalyst, we remain convinced as to the validity of our proposed mechanism.(17) The power of the phase-transfer method was revealed by a cost analysis. Although I am not at liberty to disclose the actual numbers, their relative ratios are quite interesting. If the cost of producing the racemate via the achiral phase transfer process is taken as $X/kg, the cost for producing the (S)-enantiomer was $3X by the resolution process. Employing the cinchona-alkaloid catalyst at <10 mol % in a chiral phase-transfer process afforded the (S )-isomer at a cost of $1.05X with no attempt at catalyst recycle!Speaking of Professor Corey, our paths initially crossed during work on our carbonic anhydrase program, where we needed to use the OAB (oxazaborolidine) catalyst system for enantioselective reduction of a prochiral ketone on the way to MK-417. This catalyst (19) had withstood the test of time as one of the most effective and elegant methods for enantioselective ketone reduction,(19) but clearly was applicable only to small-scale reactions based on the difficulty of purification and isolation of 19, and its poor stability to moisture. We were interested in making this catalyst system in the pilot plant and using it on the kilogram scale. Thus, we wanted a simple method for its preparation, isolation and storage. With meticulous attention to detail, we began an investigation of these issues. This resulted in a new process for the synthesis of the OAB system, and its ready isolation as a relatively stable, crystalline BH 3 adduct. (Scheme 6),(20) The preparation of the isolated complex has been described in detail in Organic Synthesis.(21) We made more than 10kg of the catalyst in the pilot plant, and have been pleased to provide samples of it tomembers of the Merck Research Labs and to friends around the world.H 2 1. COCl 22. Et 3N33333Me 2S-BH 3Xylene-Hexane Crystallize, -Me 2S OAB-BH 3 Adduct Crystalline & Stable Scheme 6: Practical process for the preparation of Corey’s OAB catalyst.One of the most remarkable programs that it has been my good fortune to work on was finasteride. The key problem in the medicinal chemistry route wasthe use of phenyl selenic anhydride to introduce the A-ring double bond. While this was a most suitable reaction at the kilogram scale, it would not be workable at the pilot scale and beyond. Ignoring the established lore, we reinvestigated the reaction of steroidal lactams with quinones and confirmed the basic research observations – no double bond introduction. This was a case where the lore was clearly correct. Noting separate papers from the Jung and Sonoda groups which reported the use of silyl enol ethers of ketones for double bond introductions in ketones that were poor substrates for quinone reactions,(22, 23) we started to add silylating agents to our reactions. With N ,O -bis-(trimethylsilyl)-trifluoroacetamide (BSTFA) we achieved a 65% yield for the reaction – far better than we could do with the selenium reagent. But, things were not so copasetic: the lactam seemed to disappear faster than the product appeared. After some fairly detailed studies we established that the silyl imidate of the steroid reacted with DDQ at room temperature, presumably via an electron-transfer reaction, to afford a mixture of lactam-DDQ adducts (20). Subsequent thermolysis afforded the desired unsaturated product (Scheme 7). Thus, we had uncovered a completely new mechanism for quinone-mediated double bond introduction that applied to both silyl imidates and silyl enol ethers: substrate-quinone adducts form via electron-transfer reactions at room temperature followed by double bond formation under thermal conditions. These observations formed the core of a very practicable approach to finasteride, once again tying together solid new science with hardcore process research. (24 ,25)t -Bu H 2CH 320Scheme 7: A new mechanism in quinone oxidation reactions.During the 90’s we foresaw a need for the enantiomers of 21, one of our lead LTD4 antagonists. The compound was proceeding in development as the racemate, despite the fact that as early as 1960 we were proceeding forward with single enantiomer drugs such as methyldopa, rather than racemates. In fact, one Merck legend states that when Max Tishler was asked whether we should proceed in development with the D,L-racemate or the single L-enantiomer of methyldopa, he responded, “Give ‘em L boys!” Back to 21 – the medicinal chemists had developed a remarkable enantioselective synthesis, but it was too complex to prepare material even at the gram level. Clearly, we needed an enzyme resolution of prochiral diester 22 (Scheme 8). Skeptics noted that such couldn’t be done as the chiral center was too far removed from the business end of the enzymatic chemistry. Bioprocess experts, on the other hand, encouraged us to pursue this avenue of research despite the lack of literature precedent. We took on the challenge and the results were everything we could expect from this gambit in bioprocess. Using a lipase from Pseudomonas a >98% e.e. was achieved in the resolution at 90% chemical yield to afford (S)-ester acid 23.(26) From this compound we could make either isomer of the target by direct amination or acid activation, amination and hydrolysis. Thus, we were able to provide quantities of both enantiomers for serious biological evaluation for the first time, and the practicality of the work was subsequently demonstrated in numerous pilot plant campaigns. Ali Shafiee has noted to me many times that this example is still cited at current symposia on enzymatic reactions as a prime example of what can be done with biotransformations.(27)2Me2H90 % yield>98 % ee21NClSSCON(CH3)2CO2H2223Me3Al1. CDI/Me2NH2. LiOH/aq THFMe2N+H2R-Amide-Acid S-Amide-AcidScheme 8: A gambit in biocatalysis.Possibly one of the most exciting programs that I have ever worked on is the Merck RT (reverse transcriptase) program which ultimately led to efavirenz. The program began with target 24, which was originally made as the reacemate and then separated into its enantiomers by chiral derivatization andchromatography.(28) Initially we developed a remarkable approach to this molecule by the quinine lithium alkoxide-mediated addition of the lithium acetylide to the imine precursor protected on nitrogen by the anthranylmethyl group. This reaction at –25°C afforded a solution e.e. of 97% in 84% chemical yield at the 1.8 kg scale (Scheme 9).(29)N NCl OProtocol:1.4 moles Acetylene1.4 moles Quinine2.8 moles BuLiAdd Imine H R = H = RT Inhibitor (24)Scale: 1.8 kg Solution e.e.: 97%Isolated Yield: 84%Figure 9. Our first enantioselective acetylide addition.As often happens, the medicinal chemists then came up with a more potent inhibitor (25, efavirenz),(28) and asked us to focus instead on it. Keeping the earlier concept in mind, we were able to achieve an e.e. in the 80’s by preforming a mixture of lithium cyclopropyl acetylide and the alkoxide of ephedrine derivative 26 in THF and then adding ketone 27 which had a p -methoxybenzyl protecting group (PMB) on nitrogen. Remembering that we had observed a remarkable temperature response in the imine addition reaction (the e.e. decreased at higher AND lower temperatures) and that the nature of lithium aggregates changes with temperature, we had the audacity to warm the THF solution of the lithium acetylide and lithium ephedrine alkoxide to 0°C, prior to cooling to <-50°C for the ketone addition. Under these conditions, we achieved a 98+% e.e. at 98% conversion (Scheme 10).(30) We later asked Dave Collum of Cornell to join us in the study of this reaction, and Dave showed by 6Li NMR studies that the equilibration produces a cubic tetramer composed of two acetylides and two alkoxides (28).(31) Dave, of course, got all of us thinking about lithium aggregation and 6Li-NMR studies, and in some NMR work of our own we showed that subsequent reaction of this tetramer with the PMB-protected ketone produces a new cubic tetramer composed of one acetylide, two ephedrine alkoxides and one product alkoxide with the product at 98+% e.e.(32) As to our interactions with Dave Collum, I can only say that he is a princeamong chemists, and he has changed the ways in which we view all lithium anion reactions.2825 Acetylide-Alkoxide ComplexScheme 10: Efaverinz and understanding enantioselective lithium alkoxide-mediated lithium acetylide additions.Wondering if the job of a process chemist is ever done, we decided to look at development of a process that would not require PMB protection and deprotection, and loss of one mole of acetylide to the product tetramer. We ended up moving to the zinc manifold recognizing problems of the unprotected substrate with strong bases and the product with strong Lewis acids. The new process that resulted was even more remarkable than the lithium acetylide process (Scheme 11). A zinc reagent mixture was prepared from diethyl zinc and the Grignard of the acetylide in the presence of the SAME ephedrine mediator and a simple achiral alcohol, and addition of the unprotected ketone at 0-25°C produced the desired product in 98% yield and 99.3% e.e. (33) Attempted mechanistic studies were not productive; however, the results of the reactions were consistent regardless of how we made up the reagent mixture.。