Elias James Corey

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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.<ref>E. J. Corey, X-M. Cheng, The Logic of Chemical Synthesis, Wiley, New York, 1995, ISBN 0-471-11594-0.</ref><ref>"The Logic of Chemical Synthesis: Multistep Synthesis of Complex Carbogenic Molecules (Nobel Lecture)" E.J. Corey, Angew. Chem. Int. Ed. Engl. 1991, 30, 455.</ref> 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.

At MIT, he earned both a bachelor's degree in 1948 and a Ph.D. in 1951. Both degrees were in chemistry. Immediately, 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.

1 Major contributions
2 Praise
3 Graduate student death
4 Woodward-Hoffmann rules
5 References
6 External links

[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.<ref>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.</ref>
t-Butyldimethylsilyl ether (TBDMS)<ref>Corey, E. J.; Venkateswarlu, A. J. Am. Chem. Soc. 1972, 94, 6190-6191. (DOI:10.1021/ja00772a043)</ref>, Triisopropylsilyl ether (TIPS), and Methoxyethoxymethyl (MEM): popular alcohol protecting groups.

Also the Corey-Bakshi-Shibata reduction stands as the most practical system for the asymmetric reduction of ketones to secondary alcohols.

[edit] Methodology

Several reactions developed in the E.J. Corey labs 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.<ref>E. J. Corey, N. M. Weinshenker, T. K. Schaaf, W. Huber, J. Am. Chem. Soc. 1969, 91, 5675-5677. (DOI:10.1021/ja01048a062)</ref><ref>K. C. Nicolaou, E. J. Sorensen, Classics in Total Synthesis, VCH, New York, 1996, ISBN 3-527-29231-4.</ref>

Image:Corey Lactone.png

Other notable syntheses include:

Longifolene<ref>Corey, E. J.; Ohno, M.; Vatakencherry, P. A.; Mitra, R. B. J. Am. Chem. Soc. 1961, 83, 1251-1253. (DOI:10.1021/ja01466a056)</ref><ref>"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)</ref>
Lactacystin<ref>"Total Synthesis of Lactacystin" Corey, E. J.; Reichard, G. A. J. Am. Chem. Soc. 1992, 114, 10677.</ref>
Miroestrol<ref>"Enantioselective Total Synthesis of Miroestrol" Corey, E. J.; Wu, L. I. J. Am. Chem. Soc. 1993, 115, 9327.</ref>
Ecteinascidin 743<ref>Corey, E. J.; Gin, D. Y.; Kania, R. S. J. Am. Chem. Soc. 1996, 118, 9202-9203.</ref>
Oseltamivir (Tamiflu) <ref>"A Short Enantioselective Pathway for the Synthesis of the Anti-Influenza Neuramidase Inhibitor Oseltamivir from 1,3-Butadiene and Acrylic Acid" Yeung, Y.-Y.; Hong, S.; Corey, E. J. J. Am. Chem. Soc. 2006, 128, 6310-6311. (DOI:10.1021/ja0616433)</ref>

[edit] Praise

Ryoji Noyori, the 2001 Nobel Prize in Chemistry laureate has commented that "without Corey, modern organic synthesis could not exist."

A press releasedescribing Corey's accomplishments following his receiving the 1990 Nobel Prize stated:

"To perform the total syntheses successfully, Corey was also obliged to develop some fifty entirely new or considerably improved synthesis reactions or reagents. It is probable that no other chemist has developed such a comprehensive and varied assortment of methods which, often showing the simplicity of genius, have become commonplace in the synthesising laboratory. His systematic use of different types of organometallic reagent has revolutionised recent techniques of synthesis in many respects."

[edit] Graduate student death

Corey has gained a certain infamy in the field of chemistry for having one graduate student commit suicide and explicitly blame the advisor (Corey) for doing so. Another suicide in his lab occurred about a year and half earlier, although the student had only been at Harvard for six months at the time and had only recently begun working for Corey.

The graduate student, Jason Altom, was a Ph.D. student at Harvard University who committed suicide by taking potassium cyanide in 1998, citing in his suicide note "abusive research supervisors" as one reason for taking his life. Altom was working on one of the most complex natural products and felt enormous pressure to finish the molecule before starting his academic career.

Altom's suicide highlighted the pressures on Ph.D. students, problems of isolation in graduate school, and sources of tension between graduate mentors and their students. His case prompted many universities to insist that Ph.D. students have an advisory committee in addition to a supervisor, to whom they might turn for support: James Anderson, who became Harvard Chemistry Department Chairman, stated that "Jason's death prompted an examination of the role the department should play in graduate students' lives". Anderson went on to promise that students will also have "confidential and seamless access" to psychological counselling services, paid for by the department. However, as of 2004, this access was completely terminated. It is unknown whether any vestiges of the department's nine-step plan toward graduate student health and happiness remain, though it was highly-publicized following Altom's suicide.

Corey, speaking of the suicide note, states: "[T]hat letter doesn't make sense. At the end, Jason must have been delusional or irrational in the extreme." Corey also is on record as stating that he never questioned Mr. Altom's intellectual contributions. "I did my best to guide Jason as a mountain guide would to guide someone climbing a mountain. I did my best every step of the way," Corey states. "My conscience is clear. Everything Jason did came out of our partnership. We never had the slightest disagreement."

The molecule on which Altom was working, aspidophytine, was subsequently completed by postdoctoral research associates and published in the Journal of the American Chemical Society in 1999 with, controversially, Altom listed as the last author (other than Corey). <ref>"Enantioselective Total Synthesis of Aspidophytine" He, F.; Bo, Y.; Altom, J. D.; Corey, E. J. J. Am. Chem. Soc. 1999, 121(28), 6771-6772. (DOI:10.1021/ja9915201)</ref>

[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.<ref>R. Hoffmann Angew. Chem. 2004, 43, 6586-6590.</ref>