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Synfacts 2009(5): 0534-0534  
DOI: 10.1055/s-0029-1216617
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Copper-Catalyzed [1,2]-Stevens Rearrangement of Sulfur Ylides

Contributor(s): Hisashi Yamamoto, Pingfan Li
J.-P. Qu, Z.-H. Xu, J. Zhou, C.-L. Cao, X.-L. Sun, L.-X. Dai, Y. Tang*
Shanghai Institute of Organic Chemistry, P. R. of China
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Publication History

Publication Date:
22 April 2009 (online)

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Significance

The first example of catalytic asymmetric [1,2]-Stevens rearrangement of 1,3-oxa­thiolanes with diazomalonates has been developed using a copper(II) triflate/bisoxazoline complex to give up to 90% ee. The reaction can be carried out under air. The usefulness of 1,2-­rearrangement for asymmetric synthesis is well demonstrated by this paper.