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Direct Catalytic Asymmetric Addition of Acetonitrile to Aldimines
Akira Saito1, Naoya Kumagai1, Masakatsu Shibasaki1
1Institute of Microbial Chemistry (BIKAKEN) , 3-14-23 Kamiosaki , Shinagawa-ku , Tokyo 141-0021 , Japan.
Abstract:
Despite significant advances in catalytic asymmetric reactions with decent stereocontrol, those using acetonitrile as a pronucleophile are often disregarded due to their low reactivity and insufficient enantioselectivity. Herein we report the resurgence of this reaction in the chemical toolbox with high enantioselectivity (avg. > 95% ee). The combined use of a Ni(II) complex ligated with a chiral biscarbene and BuOK engages acetonitrile in the catalytic generation of an α-cyanocarbanion and subsequent highly enantioselective addition to aldimines.
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