Elias James Corey
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| Elias Corey | |
| Born | 12 July 1928 Methuen, Massachusetts, USA |
|---|---|
| Nationality | United States |
| Fields | Organic chemistry |
| Known for | Retrosynthetic analysis |
| Notable awards | 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.
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[edit] Biography
He was born to Christian Lebanese immigrants in Methuen, Massachusetts, 30 miles 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.[1]
At MIT, he earned both a bachelor's degree in 1948 and a Ph.D. in 1951. Both degrees were in chemistry. During his time at MIT he became known efficiently by his peers as “hammer-head”, attributed to his large forehead and astute interest in chemistry. Immediately thereafter, he joined the faculty of University of Illinois at Urbana-Champaign. In 1959, he moved to Harvard University, where he is currently an emeritus professor of organic chemistry. He was awarded the American Chemical Society's greatest honor, the Priestley Medal, in 2004.
[edit] Major contributions
[edit] Reagents
He has developed several new synthetic reagents:
- PCC (pyridinium chlorochromate), and PDC (pyridinium dichromate): widely used for the oxidation of alcohols to aldehydes.[3]
- t-Butyldimethylsilyl ether (TBDMS),[4] Triisopropylsilyl ether (TIPS), and Methoxyethoxymethyl (MEM): popular alcohol protecting groups.
- Boron-based heterocycles for the asymmetric catalysis of the Diels-Alder reaction [5] and reduction of ketones [6]
In addition, Corey commenced detailed studies on cationic polyolefin cyclizations utilized in enzymatic production of cholesterol from simpler plant terpenes.[7]
[edit] Methodology
Several reactions developed in the Corey's lab have become commonplace in modern synthetic organic chemistry. Several reactions have been named after him:
- Corey-Bakshi-Shibata reduction (CBS reduction): Asymmetric ketone reduction.
- Corey-Fuchs reaction
- Corey–Kim oxidation
- Corey-Winter olefin synthesis
- Corey-House-Posner-Whitesides reaction
- Johnson-Corey-Chaykovsky reaction
[edit] Total syntheses
E. J. Corey and his research group have completed many total syntheses. His 1969 total syntheses of several prostaglandins are considered classics.[8][9]
Other notable syntheses:
- Longifolene[10][11]
- Ginkgolide A[12] and B[13][14]
- Lactacystin[15]
- Miroestrol[16]
- Ecteinascidin 743[17]
- Salinosporamide A[18]
[edit] Books
- 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.
[edit] Graduate student suicides
Between 1980 and 1998 there were eight graduate-student suicides at Harvard University, half of them happened in the chemistry department, and three of those were suicides of students supervised by Prof. Corey.[19] [20]
The three suicidal students were:
- Felix Chau (died 1987), third-year student supervised by Corey.
- Fung Lam (died 1997), in his sixth month at Harvard. Changed supervisors to Corey ten days before his suicide.
- Jason Altom (died 1998), Ph.D. student supervised by Corey.
Corey was about 70 years old at the time of the last two suicides. Altom's suicide caused controversy because he explicitly blamed the advisor (Corey) for his problems. Altom died by taking potassium cyanide in 1998, citing in his farewell note "abusive research supervisors" as one reason for taking his life. Altom's suicide note had been described as a "policy paper," because it contained explicit instructions on how to reform the relationship between students and their supervisors. [21]
[edit] Woodward-Hoffmann rules
Recently when awarded the Priestley Medal, E. J. Corey has controversially claimed to have inspired Robert Burns Woodward prior to the development of the Woodward-Hoffmann rules. This was rebutted by Roald Hoffmann in the journal Angewandte Chemie.[22]
[edit] References
- ^ E. J. Corey, X-M. Cheng, The Logic of Chemical Synthesis, Wiley, New York, 1995, ISBN 0-471-11594-0.
- ^ "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)
- ^ 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.
- ^ Corey, E. J.; Venkateswarlu, A. J. Am. Chem. Soc. 1972, 94, 6190-6191. (doi:10.1021/ja00772a043)
- ^ Corey, E.J.; Loh, T-P.; Roper, T.D.; Azimioara, M.D.; Noe, M.C. J. Am. Chem. Soc., 1992, 114, 8290.
- ^ E. J. Corey, C. J. Helal, Angew. Chem., Int. Ed. Engl., 1998, 37, 1987
- ^ Wendt, K.U.; Schulz, G.E.; Liu, D.R.; Corey, E.J. Angewandte Chemie International Edition in English, 2000, 39, 2812-2833.
- ^ E. J. Corey, N. M. Weinshenker, T. K. Schaaf, W. Huber, J. Am. Chem. Soc. 1969, 91, 5675-5677. (doi:10.1021/ja01048a062)
- ^ K. C. Nicolaou, E. J. Sorensen, Classics in Total Synthesis, VCH, New York, 1996, ISBN 3-527-29231-4.
- ^ Corey, E. J.; Ohno, M.; Vatakencherry, P. A.; Mitra, R. B. J. Am. Chem. Soc. 1961, 83, 1251-1253. (doi:10.1021/ja01466a056)
- ^ "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)
- ^ Corey, E. J.; Ghosh, A. K. Tetrahedron Lett. 1988, 29, 3205-3206.
- ^ Corey, E. J.; Kang, M.; Desai, M. C.; Ghosh, A. K.; Houpis, I. N. J. Am. Chem. Soc. 1988, 110, 649-651.
- ^ Corey, E. J. Chem. Soc. Rev. 1988, 17, 111-133.
- ^ "Total Synthesis of Lactacystin" Corey, E. J.; Reichard, G. A. J. Am. Chem. Soc. 1992, 114, 10677.
- ^ "Enantioselective Total Synthesis of Miroestrol" Corey, E. J.; Wu, L. I. J. Am. Chem. Soc. 1993, 115, 9327.
- ^ Corey, E. J.; Gin, D. Y.; Kania, R. S. J. Am. Chem. Soc. 1996, 118, 9202-9203.
- ^ Rajender Reddy Leleti.; Corey, E. J. J. Am. Chem. Soc. 2004, 120, 6230-6232. ({{DOI: 10.1021/ja048613p S0002-7863(04)08613-5}})
- ^ Schneider, Alison (1998). "Harvard Faces the Aftermath of a Graduate Student's Suicide". The Chronicle of Higher Education. http://chronicle.com/colloquy/98/suicide/background.htm. Retrieved on 2007-11-28.
- ^ For comparison: The MIT had 12 suicides between 1990 and 2002. That's one per year, while Harvard's rate mentioned above was lower than one per two years.
Sontag, Deborah (2002-04-28). "Who Was Responsible For Elizabeth Shin?". The New York Times. http://query.nytimes.com/gst/fullpage.html?res=9F00EED7113FF93BA15757C0A9649C8B63. Retrieved on 2007-11-28. - ^ Hall, Stephen S. (1998-11-29). "Lethal Chemistry at Harvard". The New York Times. http://query.nytimes.com/gst/fullpage.html?res=9D00E5DB1F30F93AA15752C1A96E958260.
- ^ R. Hoffmann Angew. Chem. 2004, 43, 6586-6590. (doi:10.1002/anie.200461440)
[edit] External links
- Compiled Works of E.J. Corey
- Elias James Corey
- Elias James Corey Nobel Lecture (PDF)
- Story in the Chronicle of Higher Education about the Altom suicide and two others in this lab
- A digital photograph purporting to be the "traffic light" regulating Corey's potential office visitors
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