title: N-sulfinyl amines as a nitrogen source in the asymmetric intramolecular aza-Michael reaction: total synthesis of (-)-pinidinol.
abstract: 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.
authors.affiliation: Departamento de Química Orgánica, Universidad de Valencia, 46100-Burjassot, Valencia, Spain. santos.fustero@uv.es
authors.forename: Santos
authors.initials: S
authors.lastname: Fustero
authors.forename: Silvia
authors.initials: S
authors.lastname: Monteagudo
authors.forename: María
authors.initials: M
authors.lastname: Sánchez-Roselló
authors.forename: Sonia
authors.initials: S
authors.lastname: Flores
authors.forename: Pablo
authors.initials: P
authors.lastname: Barrio
authors.forename: Carlos
authors.initials: C
authors.lastname: del Pozo
mesh_terms: 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*
chemical_list: D000588:Amines; D010880:Piperidines; D013454:Sulfoxides; C431206:pinidinol; D009584:Nitrogen