Elias James Corey


Elias James Corey
E.J. Corey

Born 12 July 1928 (1928-07-12) (age 83)
Methuen, Massachusetts, USA
Nationality United States
Fields Organic chemistry
Institutions Harvard University
Alma mater MIT
Notable students Ryōji Noyori
Known for Retrosynthetic analysis
Notable awards Franklin Medal (1978)
Wolf Prize in Chemistry (1986)
Japan Prize (1989)
Nobel Prize in Chemistry (1990)
Priestley Medal (2004)

Elias James Corey (born July 12, 1928) is an American organic chemist. In 1990 he won the Nobel Prize in Chemistry "for his development of the theory and methodology of organic synthesis", specifically retrosynthetic analysis.[1][2] Regarded by many as one of the greatest living chemists, he has developed numerous synthetic reagents, methodologies, and has advanced the science of organic synthesis considerably.

Contents

Biography

E.J. Corey was born to Christian Lebanese immigrants in Methuen, Massachusetts, 50 km (31 mi) north of Boston. His mother changed his name to "Elias" to honor his father who died eighteen months after the birth of his son. His widowed mother, brother, two sisters and an aunt and uncle all lived together in a spacious house—struggling through the depression. He attended Catholic elementary school and Lawrence Public High School.

He entered MIT in 1945. At MIT, he earned both a bachelor's degree in 1948 and a Ph.D. at age 22 in 1951. Both degrees were in chemistry. Immediately thereafter, he joined the faculty of University of Illinois at Urbana–Champaign where he became a Full Professor of Chemistry in 1956 at the age of 27. In 1959, he moved to Harvard University, where he is currently an emeritus professor of organic chemistry with an active Corey Group research program. He focuses on organic chemistry because of "its intrinsic beauty and its great relevance to human health".[3] He has been an advisor to Pfizer for more than 50 years.[4]

He and his wife, Claire, were married in 1961. They have three children, David, John, and Susan and two granddaughters, Sara and Kate Corey. Currently, he and his wife, Claire, live in Cambridge, Massachusetts.

In 1988, he was awarded the National Medal of Science.[5] He was awarded the American Chemical Society's greatest honor, the Priestley Medal, in 2004.

Major contributions

Reagents

He has developed several new synthetic reagents:

  • PCC (pyridinium chlorochromate), also referred to as the Corey-Suggs reagent, and PDC (pyridinium dichromate): widely used for the oxidation of alcohols to aldehydes.[6]
  • t-Butyldimethylsilyl ether (TBDMS),[7] Triisopropylsilyl ether (TIPS), and Methoxyethoxymethyl (MEM): popular alcohol protecting groups.
  • Boron-based heterocycles for the asymmetric catalysis of the Diels-Alder reaction[8] and reduction of ketones.[9]

In addition, Corey commenced detailed studies on cationic polyolefin cyclizations utilized in enzymatic production of cholesterol from simpler plant terpenes.[10]

Methodology

Several reactions developed in Corey's lab have become commonplace in modern synthetic organic chemistry. At least 302 methods have been developed in the Corey Group since 1950.[11] Several reactions have been named after him:

Total syntheses

E. J. Corey and his research group have completed many total syntheses. At least 265 molecules have been synthesized in the Corey Group since 1950.[12]

His 1969 total syntheses of several prostaglandins are considered classics.[13][14][15]

The Corey lactone

Other notable syntheses:

Publications

E.J. Corey has more than 1000 publications.[25] In 2002, the American Chemical Society (ACS) recognized him as the “Most Cited Author in Chemistry”. In 2007, he received the first ACS Publications Division “Cycle of Excellence High Impact Contributor Award”[26] and was ranked the number one chemist in terms of research impact by the Hirsch Index (h-index).[27]

E.J. Corey’s books include:

  • E.J. Corey and Laszlo Kurti, Enantioselective Chemical Synthesis: Methods, Logic, and Practice, Direct Book Publishing LLC, 2010, ISBN 978-0-615-39515-9
  • Elias James Corey, Xue-Min Cheng. The logic of chemical synthesis. Wiley-Interscience, 1995, ISBN 0-471-11594-0.
  • E. J. Corey, Barbara Czako, Laszlo Kurti. Molecules and Medicine John Wiley & Sons, 2008.
  • Name reactions in heterocyclic chemistry / edited by Jie-Jack Li ; scientific editor, E.J. Corey. Hoboken, N.J. : Wiley-Interscience, c2005.
  • Name reactions for functional group transformations / edited by Jie Jack Li, E.J. Corey. Hoboken, N.J. : Wiley-Interscience, c2007.

Altom suicide

Among the hundreds of graduate-students supervised by Prof. Corey was Jason Altom.[28] Altom's suicide caused controversy because he explicitly blamed Corey, his research advisor, for his suicide. Corey was devastated and bewildered by Altom's death.[29] Altom cited in his 1998 farewell note "abusive research supervisors" as one reason for taking his life. Altom's suicide note also contained explicit instructions on how to reform the relationship between students and their supervisors.[30]

The American Foundation for Suicide Prevention (AFSP) cited the New York Times article on Altom's suicide as an example of problematic reporting,[31] and suggested that Corey was unfairly scapegoated.[32] According to The Boston Globe, Altom's suicide note indicated fear that his career hopes were doomed, but The Globe also cited students and professors as saying that Altom actually retained Corey's support.[29]

Corey Group Members

As of 2010, approximately 700 people have been Corey Group members. A database of 580 former members and their current affiliation was developed for Dr. Corey’s 80th birthday in July, 2008.[33]

Woodward-Hoffmann rules

When awarded the Priestley Medal in 2004, E. J. Corey created a controversy with his claim to have inspired Robert Burns Woodward prior to the development of the Woodward-Hoffmann rules. Corey wrote:

“On May 4, 1964, I suggested to my colleague R. B. Woodward a simple explanation involving the symmetry of the perturbed (HOMO) molecular orbitals for the stereoselective cyclobutene → 1,3-butadiene and 1,3,5-hexatriene → cyclohexadiene conversions that provided the basis for the further development of these ideas into what became known as the Woodward-Hoffmann rules.”[34]

This was Corey's first public statement on his claim that starting on May 5, 1964 Woodward put forth Corey’s explanation as his own thought with no mention of Corey and the conversation of May 4. Corey had discussed his claim privately with Hoffmann and close colleagues since 1964. Corey mentions that he made the Priestley statement “so the historical record would be correct".[35]

Corey's claim and contribution were publicly rebutted by Roald Hoffmann in the journal Angewandte Chemie. In the rebuttal, Hoffmann states that he asked Corey over the course of their long discussion of the matter why Corey did not make the issue public. Corey responded that he thought such a public disagreement would hurt Harvard and that he would not “consider doing anything against Harvard, to which I was and am so devoted.” Corey also hoped that Woodward himself would correct the historical record “as he grew older, more considerate, and more sensitive to his own conscience.”[36] Woodward died suddenly of a heart attack in his sleep in 1979.

Awards

E.J. Corey has received more than 40 major awards including the Linus Pauling Award (1973), Franklin Medal (1978), Wolf Prize in Chemistry (1986), National Medal of Science (1988), Japan Prize (1989), Nobel Prize in Chemistry (1990), Roger Adams Award (1993), and the Priestley Medal (2004).[37] As of 2008, he has been awarded 19 honorary degrees from universities around the world including Oxford University (UK), Cambridge University (UK), and National Chung Cheng University.[38]

References

  1. ^ E. J. Corey, X-M. Cheng, The Logic of Chemical Synthesis, Wiley, New York, 1995, ISBN 0-471-11594-0.
  2. ^ "The Logic of Chemical Synthesis: Multistep Synthesis of Complex Carbogenic Molecules (Nobel Lecture)" E.J. Corey, Angew. Chem. Int. Ed. Engl. 1991, 30, 455. (doi:10.1002/anie.199104553)
  3. ^ Corey, E.J. (1990). "Nobel Prize Autobiography". Nobelprize.org: The Official Site of the Nobel Prize. http://nobelprize.org/nobel_prizes/chemistry/laureates/1990/corey.html. Retrieved 2010-09-09. 
  4. ^ "Compiled Works of Elias J. Corey, Photo Gallery, Pfizer Global Research". Laszlo Kurti and Jakub Svenda (webmasters). 2008-07-12. http://ejcorey.com/C1928O07RE12Y/Photoalbum/photos_main.asp?t03_placeitwastaken=Pfizer+Global+Research+and+Development&t02_yearitwastaken=2008&t01_nameofsubmitter=Pfizer. Retrieved 2010-09-09. 
  5. ^ National Science Foundation - The President's National Medal of Science
  6. ^ Corey, E.J., and Suggs, W. 'Pyridinium Chlorochromate. An Efficient Reagent for Oxidation of Primary and Secondary Alcohols to Carbonyl Compounds', Tetrahedron Lett. 1975, 31, 2647-2650.
  7. ^ Corey, E. J.; Venkateswarlu, A. J. Am. Chem. Soc. 1972, 94, 6190-6191. (doi:10.1021/ja00772a043)
  8. ^ Corey, E.J.; Loh, T-P.; Roper, T.D.; Azimioara, M.D.; Noe, M.C. J. Am. Chem. Soc., 1992, 114, 8290.
  9. ^ E. J. Corey, C. J. Helal, Angew. Chem., Int. Ed. Engl., 1998, 37, 1987
  10. ^ Wendt, K.U.; Schulz, G.E.; Liu, D.R.; Corey, E.J. Angewandte Chemie International Edition in English, 2000, 39, 2812-2833.
  11. ^ See the Methods tab"Compiled Works of Elias J. Corey". Laszlo Kurti and Jakub Svenda (webmasters). 2008-07-12. http://ejcorey.com/. Retrieved 2010-09-09. 
  12. ^ See the Syntheses tab"Compiled Works of Elias J. Corey". Laszlo Kurti and Jakub Svenda (webmasters). 2008-07-12. http://ejcorey.com/. Retrieved 2010-09-08. 
  13. ^ E. J. Corey, N. M. Weinshenker, T. K. Schaaf, W. Huber, J. Am. Chem. Soc. 1969, 91, 5675-5677. (doi:10.1021/ja01048a062)
  14. ^ K. C. Nicolaou, E. J. Sorensen, Classics in Total Synthesis, VCH, New York, 1996, ISBN 3-527-29231-4.
  15. ^ a) Corey, E. J.; Schaaf, T. K.; Huber,W.; Koelliker,V.;Weinshenker, N. M.; J. Amer. Chem. Soc. 1970, 92, 397. b) For a review see Axen, U.; Pike, J. E.; and Schneider, W. P.; in The Total Synthesis of Natural Products, Vol. 1, ApSimon, J. W., ed. Wiley, New York, 1973, 81.
  16. ^ Corey, E. J.; Ohno, M.; Vatakencherry, P. A.; Mitra, R. B. J. Am. Chem. Soc. 1961, 83, 1251-1253. (doi:10.1021/ja01466a056)
  17. ^ "Total Synthesis of Longifolene" Corey, E. J.; Ohno, M.; Mitra, R. B.; Vatakencherry, P. A. J. Am. Chem. Soc. 1964, 86, 478-485. (doi:10.1021/ja01057a039)
  18. ^ Corey, E. J.; Ghosh, A. K. Tetrahedron Lett. 1988, 29, 3205-3206.
  19. ^ Corey, E. J.; Kang, M.; Desai, M. C.; Ghosh, A. K.; Houpis, I. N. J. Am. Chem. Soc. 1988, 110, 649-651.
  20. ^ Corey, E. J. Chem. Soc. Rev. 1988, 17, 111-133.
  21. ^ "Total Synthesis of Lactacystin" Corey, E. J.; Reichard, G. A. J. Am. Chem. Soc. 1992, 114, 10677.
  22. ^ "Enantioselective Total Synthesis of Miroestrol" Corey, E. J.; Wu, L. I. J. Am. Chem. Soc. 1993, 115, 9327.
  23. ^ Corey, E. J.; Gin, D. Y.; Kania, R. S. J. Am. Chem. Soc. 1996, 118, 9202-9203.
  24. ^ Rajender Reddy Leleti.; Corey, E. J. J. Am. Chem. Soc. 2004, 120, 6230-6232. ({{DOI: 10.1021/ja048613p S0002-7863(04)08613-5}})
  25. ^ See the Publications tab"Compiled Works of Elias J. Corey". Laszlo Kurti and Jakub Svenda (webmasters). 2008-07-12. http://ejcorey.com/. Retrieved 2010-09-08. 
  26. ^ Baum, Rudy (2007-08-21). "E.J. Corey: Chemist Extraordinaire". C&EN Meeting Weblog, 234th ACS National Meeting &Exposition, August 19–23, 2007, Boston, MA.. http://cenboston.wordpress.com/2007/08/21/ej-corey-chemist-extraordinaire/. Retrieved 2010-09-08. 
  27. ^ Van Noorden, Richard (2007-04-23). "Hirsch index ranks top chemists". RSC: Advancing the Chemical Sciences, Chemistry World. http://www.rsc.org/chemistryworld/News/2007/April/23040701.asp. Retrieved 2010-09-09. 
  28. ^ Schneider, Alison (1998). "Harvard Faces the Aftermath of a Graduate Student's Suicide". The Chronicle of Higher Education. http://chronicle.com/article/Harvard-Faces-the-Aftermath-of/6469/. Retrieved 2010-08-21. 
  29. ^ a b English, Bella. "Grad-student suicides spur big changes at Harvard chem labs", Boston Globe via Archive.org (2001-01-02).
  30. ^ Hall, Stephen S. (1998-11-29). "Lethal Chemistry at Harvard". The New York Times. http://query.nytimes.com/gst/fullpage.html?res=9D00E5DB1F30F93AA15752C1A96E958260. 
  31. ^ "For the Media: Examples of Good and Problematic Reporting, Scapegoating, New York Times Magazine: Lethal Chemistry at Harvard". American Foundation for Suicide Prevention (AFSP). 2010. http://www.afsp.org/index.cfm?fuseaction=home.viewPage&page_id=7837B90F-C3D2-D5C5-6F1CBC3E73512E10. Retrieved 2010-08-21. 
  32. ^ The AFSP incorrectly identifies the author and date of the New York Times article as Keith B. Richburg and November 28, 1998. The author was Stephen S. Hall and the date of publication was November 29, 1998.H, H; M.A. (2010). "For the Media: Problematic Reporting, Scapegoating". American Foundation for Suicide Prevention (AFSP). http://www.afsp.org/index.cfm?fuseaction=home.viewpage&page_id=92569BDA-A491-50C6-17ED3B1618AF3291. Retrieved 2010-08-21. 
  33. ^ See the Members' Data tab"Compiled Works of Elias J. Corey". Laszlo Kurti and Jakub Svenda (webmasters). 2008-07-12. http://ejcorey.com/. Retrieved 2010-08-20. 
  34. ^ See the E.J. Corey, Impossible Dreams tabCorey, E.J. (Volume 69, Number 9, April 30, 2004). "Impossible Dreams". JOC Perspective. pp. 2917–2919. http://ejcorey.com/. Retrieved 2010-09-10. 
  35. ^ This article is also reprinted at http://www.facebook.com/topic.php?uid=112913412086700&topic=31Johnson, Carolyn Y. (March 1, 2005). "Whose idea was it?". Boston Globe. http://www.boston.com/news/globe/health_science/articles/2005/03/01/whose_idea_was_it?pg=2. Retrieved 2010-09-10. 
  36. ^ Hoffman, Roald (Volume 43, Issue 48, December 10, 2004). A Claim on the Development of the Frontier Orbital Explanation Electrocyclic Reactions. Angewandte Chemie International Edition. pp. 6586–6590. doi:10.1002/anie.200461440. 
  37. ^ See the E.J. Corey, Major Awards tab"Compiled Works of Elias J. Corey". Laszlo Kurti and Jakub Svenda (webmasters). 2008-07-12. http://ejcorey.com/. Retrieved 2010-09-09. 
  38. ^ See the E.J. Corey, Honorary Degrees tab"Compiled Works of Elias J. Corey". Laszlo Kurti and Jakub Svenda (webmasters). 2008-07-12. http://ejcorey.com/. Retrieved 2010-09-08. 

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  • Elias James Corey — (* 12. Juli 1928 in Methuen, Massachusetts) ist ein US amerikanischer Chemiker libanesischer Herkunft und emeritierter Professor an der Harvard University. 1990 erhielt er den Nobelpreis für Chemie für die Entwicklung der Theorie und Methodik der …   Deutsch Wikipedia

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  • Corey,Elias James — Cor·ey (kôrʹē), Elias James. Born 1928. American chemist. He won a 1990 Nobel Prize for developing techniques of creating synthetic compounds. * * * …   Universalium

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