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

An alpha-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 alpha-chiral acyclic nitrile carbanion that has been considered to be very configurationally labile.