Title | Highly enantioselective, catalytic conjugate addition of cyanide to alpha,beta-unsaturated imides. |
Publication Type | Journal Article |
Year of Publication | 2003 |
Authors | Sammis, GM, Jacobsen, EN |
Journal | Journal of the American Chemical Society |
Volume | 125 |
Pagination | 4442-3 |
Date Published | 2003 Apr 16 |
ISSN | 0002-7863 |
Keywords | ALKENES, 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. |