Literature DB >> 19685927

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

Charles P Allen1, Tamas Benkovics, Amanda K Turek, Tehshik P Yoon.   

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.

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Year:  2009        PMID: 19685927      PMCID: PMC2737076          DOI: 10.1021/ja906183g

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  14 in total

1.  Polyfluorinated Oxaziridines: Synthesis and Reactivity.

Authors:  Viacheslav A. Petrov; Giuseppe Resnati
Journal:  Chem Rev       Date:  1996-08-01       Impact factor: 60.622

2.  Enantioselective catalytic aziridinations and asymmetric nitrene insertions into CH bonds.

Authors:  Paul Müller; Corinne Fruit
Journal:  Chem Rev       Date:  2003-08       Impact factor: 60.622

3.  Chemistry of dioxiranes. 4. Oxygen atom insertion into carbon-hydrogen bonds by dimethyldioxirane.

Authors:  R W Murray; R Jeyaraman; L Mohan
Journal:  J Am Chem Soc       Date:  1986-04-01       Impact factor: 15.419

4.  Copper(II)-catalyzed aminohydroxylation of olefins.

Authors:  David J Michaelis; Christopher J Shaffer; Tehshik P Yoon
Journal:  J Am Chem Soc       Date:  2007-01-30       Impact factor: 15.419

5.  Synthetic applications of nonmetal catalysts for homogeneous oxidations.

Authors:  W Adam; C R Saha-Möller; P A Ganeshpure
Journal:  Chem Rev       Date:  2001-11       Impact factor: 60.622

6.  Oxaziridine-mediated catalytic hydroxylation of unactivated 3 degrees C-H bonds using hydrogen peroxide.

Authors:  Benjamin H Brodsky; J Du Bois
Journal:  J Am Chem Soc       Date:  2005-11-09       Impact factor: 15.419

7.  Cycloadditions of N-sulfonyl nitrones generated by lewis acid catalyzed rearrangement of oxaziridines.

Authors:  Katherine M Partridge; Mary E Anzovino; Tehshik P Yoon
Journal:  J Am Chem Soc       Date:  2008-02-15       Impact factor: 15.419

8.  Investigation on the regioselectivities of intramolecular oxidation of unactivated C-H bonds by dioxiranes generated in situ.

Authors:  Man-Kin Wong; Nga-Wai Chung; Lan He; Xue-Chao Wang; Zheng Yan; Yeung-Chiu Tang; Dan Yang
Journal:  J Org Chem       Date:  2003-08-08       Impact factor: 4.354

Review 9.  Catalytic C-H functionalization by metal carbenoid and nitrenoid insertion.

Authors:  Huw M L Davies; James R Manning
Journal:  Nature       Date:  2008-01-24       Impact factor: 49.962

10.  Anionic halocuprate(II) complexes as catalysts for the oxaziridine-mediated aminohydroxylation of olefins.

Authors:  Tamas Benkovics; Juana Du; Ilia A Guzei; Tehshik P Yoon
Journal:  J Org Chem       Date:  2009-08-07       Impact factor: 4.354

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  4 in total

Review 1.  If C-H bonds could talk: selective C-H bond oxidation.

Authors:  Timothy Newhouse; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2011-03-16       Impact factor: 15.336

2.  C-H bond functionalization via hydride transfer: formation of α-arylated piperidines and 1,2,3,4-tetrahydroisoquinolines via stereoselective intramolecular amination of benzylic C-H bonds.

Authors:  Paul A Vadola; Ignacio Carrera; Dalibor Sames
Journal:  J Org Chem       Date:  2012-06-06       Impact factor: 4.354

3.  Advances in the chemistry of oxaziridines.

Authors:  Kevin S Williamson; David J Michaelis; Tehshik P Yoon
Journal:  Chem Rev       Date:  2014-04-22       Impact factor: 60.622

Review 4.  Recent Advances in the Catalytic Asymmetric Reactions of Oxaziridines.

Authors:  Qiao Ren; Wen Yang; Yunfei Lan; Xurong Qin; Youzhou He; Lujiang Yuan
Journal:  Molecules       Date:  2018-10-16       Impact factor: 4.411

  4 in total

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