Literature DB >> 16674092

Oxaziridine-mediated amination of branched allylic sulfides: stereospecific formation of allylic amine derivatives via [2,3]-sigmatropic rearrangement.

Alan Armstrong1, Lee Challinor, Richard S Cooke, Jennifer H Moir, Nigel R Treweeke.   

Abstract

Reaction of branched allylic sulfides with the N-Boc-oxaziridine 1 results in [2,3]-sigmatropic rearrangement of the intermediate allylic N-Boc-sulfimides with a high level of chirality transfer. The first example of formation of a quaternary stereocenter using this transformation is reported.

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Year:  2006        PMID: 16674092     DOI: 10.1021/jo060369s

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  2 in total

1.  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 2.  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

  2 in total

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