|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|
|Date Published||2003 Apr 16|
|Keywords||ALKENES, amino acids, CATALYSIS, CYANIDES, gamma-Aminobutyric Acid, Imides, Stereoisomerism|
(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.