Oxaziridine-mediated intramolecular amination of sp(3)-hybridized C-H bonds.
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.
Allen
Charles P
CP
Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706, USA.
Benkovics
Tamas
T
Turek
Amanda K
AK
Yoon
Tehshik P
TP
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
D001388:Aziridines; D002244:Carbon; D003300:Copper; D006859:Hydrogen
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