title: Synthesis of enantiopure substituted piperidines via an aziridinium ring expansion.
abstract: Herein we report a novel methodology for the asymmetric synthesis of 3-substituted piperidines from readily available chiral building blocks. This method, which features a novel irreversible dihydropyrole-tetrahydropyridine ring expansion, allows the introduction of a large variety of substituents at the 3-position and permits substitution at the 2- and 6-position giving mono-, di-, or trisubstituted piperidines with high diastereocontrol.
authors.affiliation: Department of Chemistry, Université de Montréal, P.O. Box 6128, Station Downtown, Montreal, Quebec, Canada, H3C 3J7.
authors.forename: Scott B D
authors.initials: SB
authors.lastname: Jarvis
authors.forename: Andre B
authors.initials: AB
authors.lastname: Charette
mesh_terms: D001388:Aziridines / Q000737:chemistry*; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D001388:Aziridines; D010880:Piperidines; C033132:aziridine