N-Sulfinyl Amines as a Nitrogen Source in the Asymmetric Intramolecular Aza-Michael Reaction: Total Synthesis of (-)-Pinidinol

N-Sulfinyl amines have been successfully employed as nitrogen nucleophiles for the asymmetric intramolecular aza-Michael reaction. The synthetic strategy involves a cross-metathesis reaction followed by the Michael-type cyclization. either in a base-catalyzed two-step procedure or in a tandem fashion The (developed methodology allows access to chiral substituted pyrrolidines and piperidines bearing one or two stereocenters and it has been applied to the synthesis of the piperidine alkaloid (-)-pinidinol