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The Catalytic Acylcyanation of Imines
Author(s) -
Pan Subhas Chandra,
List Benjamin
Publication year - 2008
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.200700327
Subject(s) - strecker amino acid synthesis , enantioselective synthesis , imine , aldimine , catalysis , thiourea , chemistry , organocatalysis , amidine , organic chemistry , combinatorial chemistry
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.