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.
Fustero, Santos,Monteagudo, Silvia,Sanchez-Rosello, Maria,Flores, Sonia,Barrio, Pablo,Del Pozo, Carlos