Journal
CHEMISTRY-AN ASIAN JOURNAL
Volume 3, Issue 2, Pages 430-437Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.200700327
Keywords
acylcyanation; enantioselectivity; imines; multicomponent reactions; organocatalysis
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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 a-amino carbonyl framework. Furthermore, a novel cyclic amidine was obtained from the reaction of acetyl cyanide with ketimines.
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