Highly enantioselective, catalytic conjugate addition of cyanide to alpha,beta-unsaturated imides.
(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.
Sammis
Glenn M
GM
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA 02138, USA.
Jacobsen
Eric N
EN
D000475:Alkenes / Q000737:chemistry; D000596:Amino Acids / Q000138:chemical synthesis; D002384:Catalysis; D003486:Cyanides / Q000138:chemical synthesis / Q000737:chemistry*; D007094:Imides / Q000138:chemical synthesis / Q000737:chemistry*; D000069583:Pregabalin; D013237:Stereoisomerism; D005680:gamma-Aminobutyric Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis
D000475:Alkenes; D000596:Amino Acids; D003486:Cyanides; D007094:Imides; D000069583:Pregabalin; D005680:gamma-Aminobutyric Acid