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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.

SUBMITTER: Allen CP

PROVIDER: S-EPMC2737076 | biostudies-literature | 2009 Sep

REPOSITORIES: biostudies-literature

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Oxaziridine-mediated intramolecular amination of sp(3)-hybridized C-H bonds.

Allen Charles P CP Benkovics Tamas T Turek Amanda K AK Yoon Tehshik P TP

Journal of the American Chemical Society 20090901 35

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 c ...[more]

PMID: 19685927

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