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Synfacts 2007(9): 0960-0960  
DOI: 10.1055/s-2007-968848
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Desymmetrization of meso-Epoxides by Sulfur Nucleophiles

Contributor(s): Mark Lautens, Michael Langer
M. V. Nandakumar, A. Tschöp, H. Krautscheid, C. Schneider*
Universität Leipzig, Germany
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Publication History

Publication Date:
23 August 2007 (online)

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Significance

The desymmetrization of meso-epo­xides by nucleophilic attack has proven to be a viable method in the synthesis of 1,2-difunctionalized compounds. In this paper, the authors present the extension of their chiral Lewis acid mediated ring opening of meso-epoxides to sulfur nucleophiles. The anti-configured 1,2-thio alcohols can be obtained in high yields and ee.