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A Highly Tunable Stereoselective Olefination of Semistabilized Triphenylphosphonium Ylides with N-Sulfonyl Imines

De-Jun Dong, Hai-Hua Li and Shi-Kai Tian*

*Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, China, Email: tianskustc.edu.cn

D.-J. Dong, H.-H. Li, S.-K. Tian, J. Am. Chem. Soc., 2010, 132, 5018-5020.

DOI: 10.1021/ja910238f (free Supporting Information)



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Abstract

N-sulfonyl imines undergo olefination reactions with various benzylidenetriphenylphosphoranes or allylidenetriphenylphosphoranes under mild reaction conditions to afford an array of both Z- and E-isomers of conjugated alkenes in good to excellent yields and with greater than 99:1 stereoselectivity depending on the N-sulfonyl group.

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Key Words

Wittig Reaction, Z-Alkenes, E-Alkenes, Dienes


ID: J48-Y2010-0970