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Synfacts 2006(2): 0129-0129  
DOI: 10.1055/s-2005-924811
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

[2,3]-Sigmatropic Rearrangement of Sulfur Ylides

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
M. Ma, L. Peng, C. Li, X. Zhang, J. Wang*
Peking University, P. R. of China
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Publication History

Publication Date:
23 January 2006 (online)

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Significance

The [2,3]-sigmatropic rearrangement of sulfur ylides is an important class of reactions in that simultaneous formation of a carbon-carbon and carbon-sulfur bond can be achieved. This paper reports the necessity of a chiral auxillary based on Oppolzer’s sultam for the stereoselective reaction. The formation of homoallyl sulfides as well as the formation of allenes was found to proceed with high levels of enantioselectivity (>90% ee in most cases).