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Transcript
Highly Cited Contributions From
EJ Corey
John Hayes
Group Meeting Special Topic
8/26/15
Biography
•
•
•
•
Born July 12, 1928
Undergrad: MIT
Ph.D.: MIT, John C. Sheehan
1956: University of Illinois,
Urbana-Champaign
• 1959: Harvard University
• Awards
• Notable Students
Scope of Accomplishments
• 1105 publications in 2014 (+ 7 not updated)
– Ejcorey.org
• 17 Unique Methods Between 1950 and 2003
– Including: Corey-Chaykovsky, PCC Oxidation
• >260 Total Syntheses
• At least 5 books with numerous forewords authored
Corey-Bakshi-Shibata (CBS) Reagent
Corey, E.J., JACS, 1987, 109, 5551.
TBS Protecting Group
• Orthogonal to -OBn, Otrichloroethyl, and
tetrahydropyran (THP)
• More stable silyl ether than TMS
and dimethylisopropylsilyl ether
• First time used imidazole and DMF
Corey, E.J., JACS, 1972, 94, 6190.
Corey-Chaykovsky Reaction
• First use in ring expansions and
homologations
• Dimethyloxosulfonium vs.
Dimethylsulfonium
Corey, E.J., JACS, 1965, 87, 1353.
Enantioselective Phase Transfer Catalysis
Corey, E.J., JACS, 1997, 119, 12414.
Corey-Fuchs Reaction
• Conversion of aldehydes to
terminal alkynes
• 1st Step: Wittig with CBr4
• 2nd Step: Deprotonation and
Lithium-Halogen Exchange
Corey, E.J., Tet. Lett., 1972, 13, 3769.
PCC Oxidation
Corey, E.J., Tet. Lett., 1975, 31, 2647.
Enantioselective Synthesis of α-Amino Nitriles
Corey, E.J., Org. Lett., 1999, 1, 157.
Catalyst for Enantioselective Diels-Alder
• Catalyst produced in 3 steps
from (S)-(+)-Phenylglycinol
• Diels-Alder experiments
performed using Fe(III)
halides with 4 and
cyclopentadiene
Corey, E.J., JACS, 1991, 113, 729.
Enantioselective Synthesis of Amino Acids by
Chiral Phase Transfer Catalyst
Corey, E.J., Tet. Lett., 1998, 39, 5347.
PDC Oxidation
Corey, E.J., Tet. Lett., 1979, 5, 399.
Face-Selective Nitroaldol
Corey, E.J., ACIE, 1999, 111, 2057.
Enantioselective Total Synthesis of Ecteinascidin 743
Corey, E.J., JACS,
1996, 118, 9202.
CuCl Accelerated Stille Couplings
Corey, E.J., JACS, 1999, 121, 7600.
Silylations with Trialkylsilyltriflates
• New method for producing
TBSOTf and TIPSOTf
• Use of TBSOTf to silylate tertiary
and unreactive secondary alcohols
• Use of TIPSOTf to trap enol ethers
• Improvement of silylation
procedures for C18 HPLC columns
Corey, E.J., Tet. Lett., 1981, 82, 3455.
Oxidative Hydrolysis of Dithianes to Carbonyls
Corey, E.J., JOC, 1971, 36, 3553.
Acetoxylation and C-C Bond Formation at
Unactivated Positions on α-Amino Acids
Corey, E.J., Org. Lett., 2006, 8, 3391.
Enantioselective Route to (S)-(-)-phenyloxirane
Corey, E.J., JOC, 1988, 53, 2861.
Corey-Nicolaou Macrolactonization
Corey, E.J., JACS, 1974, 96, 5614.
Enantioselective Diels-Alder and Aldol Reactions
Corey, E.J., JACS, 1989, 111, 5493.
Enantioselective Epoxidation of α,ß-Enones
Corey, E.J., Org. Lett., 1999, 1, 1287.
Super-Lewis Acidic Chiral Catalyst
Corey, E.J., JACS, 1996, 118, 5502.
Highly Cited Contributions From
EJ Corey
John Hayes
Group Meeting Special Topic
8/26/15