The catalytic acylcyanation of imines.
The catalytic acylcyanation of aldimines with acylcyanides and a direct three-component variant involving the generation of an imine in situ have been developed. Furthermore, a highly enantioselective version has been established, culminating in the first organocatalytic asymmetric three-component Strecker reaction. Jacobsen thiourea catalysts were found to catalyze the reaction with excellent enantioselectivities, whereas binol phosphates (binol = 1,1'-bi-2,2'-naphthol) proved to be catalytically active but only modestly enantioselective. A large number of different substrates could be used in the processes described, thus illustrating the potential of our reaction for the generation of diversity within the attractive alpha-amino carbonyl framework. Furthermore, a novel cyclic amidine was obtained from the reaction of acetyl cyanide with ketimines.
Pan
Subhas Chandra
SC
Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany.
List
Benjamin
B
D000107:Acetylation; D000215:Acylation; D000447:Aldehydes / Q000737:chemistry; D000578:Amidines / Q000737:chemistry; D000588:Amines / Q000737:chemistry; D001554:Benzene / Q000737:chemistry; D002384:Catalysis; D003486:Cyanides / Q000737:chemistry*; D007097:Imines / Q000138:chemical synthesis* / Q000737:chemistry; D007477:Ions / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D014867:Water / Q000737:chemistry
D000447:Aldehydes; D000578:Amidines; D000588:Amines; D003486:Cyanides; D007097:Imines; D007477:Ions; D014867:Water; D001554:Benzene