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
S
Departamento de Química Orgánica, Universidad de Valencia, 46100-Burjassot, Valencia, Spain. santos.fustero@uv.es
Monteagudo
Silvia
S
Sánchez-Roselló
María
M
Flores
Sonia
S
Barrio
Pablo
P
del Pozo
Carlos
C
D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013454:Sulfoxides / Q000737:chemistry*
D000588:Amines; D010880:Piperidines; D013454:Sulfoxides; C431206:pinidinol; D009584:Nitrogen