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Highly enantioselective, catalytic conjugate addition of cyanide to alpha,beta-unsaturated imides.

TitleHighly enantioselective, catalytic conjugate addition of cyanide to alpha,beta-unsaturated imides.
Publication TypeJournal Article
Year of Publication2003
AuthorsSammis, GM, Jacobsen, EN
JournalJournal of the American Chemical Society
Volume125
Pagination4442-3
Date Published2003 Apr 16
ISSN0002-7863
KeywordsALKENES, amino acids, CATALYSIS, CYANIDES, gamma-Aminobutyric Acid, Imides, Stereoisomerism
Abstract

(Salen)Al-Cl complex 1a catalyzes the asymmetric conjugate addition of hydrogen cyanide to alpha,beta-unsaturated imides in high yields and enantioselectivities. The cyanide adducts can readily be converted into a variety of useful chiral building blocks, including alpha-substituted-beta-amino acids and beta-substituted-gamma-aminobutyric acids. Mechanistic data obtained thus far point to a cooperative bimetallic mechanism for nucleophile and electrophile activation.