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Organocatalytic Asymmetric Sulfa-Michael Addition of Thiols to α,β-Unsaturated Hexafluoroisopropyl Esters: Expeditious Access to (R)-Thiazesim

Xin Fang, Jun Li and Chun-Jiang Wang*

*College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072, China, Email: cjwangwhu.edu.cn

X. Fang, J. Li, C.-J. Wang, Org. Lett., 2013, 15, 3448-3451.

DOI: 10.1021/ol4015305


Abstract

A highly efficient organocatalytic asymmetric sulfa-Michael addition of thiols to hexafluoroisopropyl α,β-unsaturated esters performs well over a broad scope of α,β-unsaturated esters and diversified thiols. Introducing electron-withdrawing hexafluoroisopropyl ester is crucial to enhancing the electrophilicity of unsaturated esters as Michael acceptors.


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Key Words

1,4-addition, organocatalysis


ID: J54-Y2013