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The Catalytic Acylcyanation of Imines

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Pan,  Subhas Chandra
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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List,  Benjamin
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Pan, S. C., & List, B. (2008). The Catalytic Acylcyanation of Imines. Chemistry – An Asian Journal, 3(2), 430-437. doi:10.1002/asia.200700327.


Cite as: http://hdl.handle.net/11858/00-001M-0000-000F-9057-5
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.