title: Oxaziridine-mediated intramolecular amination of sp(3)-hybridized C-H bonds.
abstract: We describe a new oxaziridine-mediated approach to the amination of sp(3)-hybridized C-H bonds. In the presence of a copper(II) catalyst, N-sulfonyl oxaziridines participate in efficient intramolecular cyclization reactions to afford a variety of piperidine and tetrahydroisoquinoline structures. The aminal intermediates provide a convenient functional handle for further elaboration of these structures, demonstrating the utility of this new methodology for the rapid construction of structurally complex nitrogen-containing heterocycles.
authors.affiliation: Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706, USA.
authors.forename: Charles P
authors.initials: CP
authors.lastname: Allen
authors.forename: Tamas
authors.initials: T
authors.lastname: Benkovics
authors.forename: Amanda K
authors.initials: AK
authors.lastname: Turek
authors.forename: Tehshik P
authors.initials: TP
authors.lastname: Yoon
mesh_terms: D000586:Amination; D001388:Aziridines / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D006859:Hydrogen / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D001388:Aziridines; D002244:Carbon; D003300:Copper; D006859:Hydrogen
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