title: Tantalum catalyzed hydroaminoalkylation for the synthesis of α- and β-substituted N-heterocycles.
abstract: Unprotected secondary amines are directly alkylated by C-H functionalization adjacent to nitrogen, thereby opening new routes toward the synthesis of α- and β-alkylated N-heterocycles. α-Alkylated piperidine, piperazine, and azepane products are prepared from heterocycles and alkenes in an atom-economic reaction with excellent regio- and diastereoselectivity. β-Alkylated N-heterocycles are synthesized via a scalable one-pot alkylation/cyclization procedure generating 3-methylated azetidines, pyrrolidines, and piperidines.
authors.affiliation: Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, B.C, Canada, V6T 1Z1.
authors.forename: Philippa R
authors.initials: PR
authors.lastname: Payne
authors.forename: Pierre
authors.initials: P
authors.lastname: Garcia
authors.forename: Patrick
authors.initials: P
authors.lastname: Eisenberger
authors.forename: Jacky C-H
authors.initials: JC
authors.lastname: Yim
authors.forename: Laurel L
authors.initials: LL
authors.lastname: Schafer
mesh_terms: D000478:Alkylation; D001384:Azetidines / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013635:Tantalum / Q000737:chemistry*
chemical_list: D001384:Azetidines; D006571:Heterocyclic Compounds; D010880:Piperidines; D011759:Pyrrolidines; D013635:Tantalum