Highly Enantioselective, Catalytic Conjugate Addition of Cyanide to α,β-Unsaturated Imides
- 25 March 2003
- journal article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 125 (15) , 4442-4443
- https://doi.org/10.1021/ja034635k
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.Keywords
This publication has 3 references indexed in Scilit:
- Potent and stereospecific anticonvulsant activity of 3-isobutyl GABA relates to in vitro binding at a novel site labeled by tritiated gabapentinEpilepsy Research, 1993
- Chemoenzymatic Synthesis of (R)- and (S)-4-Amino-3-Methylbutanoic AcidsSynthetic Communications, 1990
- Phosphorus in organic synthesis—VIITetrahedron, 1974