Addition of alpha-aminonitriles to alpha,beta-unsaturated carbonyl compounds : a one-pot synthesis of polysubstituted pyrrolidines

The vinylogous addition of deprotonated N-alkyl-alpha-aminonitriles to alpha,beta-unsaturated carbonyl compounds yields cyclic intermediates which can be reduced to form polysubstituted pyrrolidines in a one-pot reaction sequence. Since the cyano substituent is lost in the reduction step, the aminonitriles serve as easily accessible (N-alkylamino)-substituted carbanion equivalents