One-Pot Synthesis of Polysubstituted Pyrrolidines from Aminonitriles
21 February 2005 (eFirst)
α-Aminonitriles with a mono- or unsubstituted amino group as well as α-(alkylideneamino)nitriles can be employed as easily accessible α-aminocarbanion equivalents. Their α-deprotonation yields stabilized carbanions, which undergo smooth 1,4-addition to α,β-unsaturated carbonyl compounds. The resulting δ-keto-α-aminonitriles can be reductively cyclized to form polysubstituted pyrrolidines.
pyrrolidines - aminonitriles - Michael additions - reductions - combinatorial chemistry