Enantioselective trapping of an α-chiral carbanion of acyclic nitrile by a carbon electrophile.

Chem Commun (Camb)

Department of Synthetic Organic Chemistry, Graduate School of Biomedical Sciences, Hiroshima University, 1-2-3 Kasumi, Minami-Ku, Hiroshima, 734-8553, Japan.

Published: March 2012

An α-chiral nitrile carbanion generated by deprotonation of enantioenriched O-carbamoyl cyanohydrin was trapped in situ with ethyl cyanoformate to give the corresponding ester derivative in 92% yield and 90 : 10 er, providing the first example of trapping of an α-chiral acyclic nitrile carbanion that has been considered to be very configurationally labile.

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http://dx.doi.org/10.1039/c2cc00082bDOI Listing

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