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Free keywords:
acylcyanation; enantioselectivity; imines; multicomponent reactions; organocatalysis
Abstract:
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 α‐amino carbonyl framework. Furthermore, a novel cyclic amidine was obtained from the reaction of acetyl cyanide with ketimines.
