Elias James Corey

Encyclopedia : E : EL : ELI : Elias James Corey

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.E. J. Corey, X-M. Cheng, The Logic of Chemical Synthesis, Wiley, New York, 1995, ISBN 0471115940."The Logic of Chemical Synthesis: Multistep Synthesis of Complex Carbogenic Molecules (Nobel Lecture)" E.J. Corey, Angew. Chem. Int. Ed. Engl. 1991, 30, 455. 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. 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.

Major contributions

Reagents

• PCC (pyridinium chlorochromate), and PDC (pyridinium dichromate): widely used for the oxidation of alcohols to aldehydes.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.
• t-Butyldimethylsilyl ether (TBDMS)Corey, E. J.; Venkateswarlu, A. J. Am. Chem. Soc. 1972, 94, 6190-6191., Triisopropylsilyl ether (TIPS), and Methoxyethoxymethyl (MEM): popular alcohol protecting groups.

Methodology

• 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

Total syntheses

Other notable syntheses include:

• LongifoleneCorey, E. J. et al. J. Am. Chem. Soc. 1961, 83, 1251.Corey, E. J. et al. J. Am. Chem. Soc. 1964, 86, 478.
• Lactacystin"Total Synthesis of Lactacystin" Corey, E. J.; Reichard, G. A. J. Am. Chem. Soc. 1992, 114, 10677.
• Miroestrol"Enantioselective Total Synthesis of Miroestrol" Corey, E. J.; Wu, L. I. J. Am. Chem. Soc. 1993, 115, 9327.
• Ecteinascidin 743Corey, E. J.; Gin, D. Y.; Kania, R. S. J. Am. Chem. Soc. 1996, 118, 9202-9203.
• Salinosporamide"A Simple Stereocontrolled Synthesis of Salinosporamide A" Reddy, L. R.; Saravanan, P.; Corey, E. J. J. Am. Chem. Soc. 2004, 126, 6230 [(abstract)].
• Oseltamivir (Tamiflu) A Short Enantioselective Pathway for the Synthesis of the Anti-Influenza Neuramidase Inhibitor Oseltamivir from 1,3-Butadiene and Acrylic Acid Ying-Yeung Yeung, Sungwoo Hong, and E. J. Corey J. Am. Chem. Soc.; 2006; ASAP Web Release Date: 25-Apr-2006; (Communication) [Abstract]

Praise

A [press release]describing 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."

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."

Interestingly, the synthesis of the molecule Altom was working on at the time of his death in 1998 has yet to be completed in 2006, eight years later. Some see this as an indication of the difficulty associated with this project and of the unrealistic expectations that the student may have place upon himself at the time.

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.R. Hoffmann Angew. Chem. 2004, 43, 6586-6590.

References

External links

• [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]

From Wikipedia, the Free Encyclopedia. Original article here. Support Wikipedia by contributing or donating.
All text is available under the terms of the GNU Free Documentation License See Wikipedia Copyrights for details.