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Synlett 2011(13): 1789-1792  
DOI: 10.1055/s-0030-1260962
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© Georg Thieme Verlag Stuttgart ˙ New York

Stereoselective [2,3]-Rearrangements of Amine N-Oxides

Hongli Bao, Xiangbing Qi, Uttam K. Tambar*
Department of Biochemistry, Division of Chemistry, The University of Texas Southwestern Medical Center at Dallas, 5323 Harry Hines Boulevard, Dallas, TX 75390-9038, USA
Fax: +1(214)6488856; e-Mail: Uttam.Tambar@utsouthwestern.edu;
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Publication History

Received 12 April 2011
Publication Date:
21 July 2011 (online)

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Abstract

Despite the long history of [2,3]-sigmatropic rearrangements, there are surprisingly few catalytic and enantioselective variants of these transformations. This article describes the most common strategies developed for stereoselective [2,3]-rearrangements of amine N-oxides (Meisenheimer rearrangement), including our recently reported palladium-catalyzed enantioselective process.

Key words

rearrangement - palladium - asymmetric catalysis - pericyclic reaction - amine N-oxide

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