Enantioselective Synthesis of Trifluoromethylated Tertiary Thioethers through Organocatalytic Sulfa-Michael Addition of Thiols to β-Trifluoromethyl β,β-Disubstituted Enones

Yao-Feng Wang; Shaoxiang Wu; Pran Gopal Karmaker; Muhammad Sohail; Qi Wang; Fu-Xue Chen

doi:10.1055/s-0034-1380138

Synthesis, Table of Contents

Synthesis 2015; 47(08): 1147-1153
DOI: 10.1055/s-0034-1380138

paper

Enantioselective Synthesis of Trifluoromethylated Tertiary Thioethers through Organocatalytic Sulfa-Michael Addition of Thiols to β-Trifluoromethyl β,β-Disubstituted Enones

Yao-Feng Wang

^aSchool of Chemical Engineering and the Environment, Beijing Institute of Technology, 5 South Zhongguancun Street, Haidian District, Beijing 100081, P. R. of China

,

Shaoxiang Wu

^bNutrichem Company Limited, Building D-1, Zhongguancun Dongsheng Science Park, No.66 Xixiaokou Road, Haidian District, Beijing 100192, P. R. of China Email: fuxue.chen@bit.edu.cn

,

Pran Gopal Karmaker

^aSchool of Chemical Engineering and the Environment, Beijing Institute of Technology, 5 South Zhongguancun Street, Haidian District, Beijing 100081, P. R. of China

,

Muhammad Sohail

^aSchool of Chemical Engineering and the Environment, Beijing Institute of Technology, 5 South Zhongguancun Street, Haidian District, Beijing 100081, P. R. of China

,

Qi Wang

^aSchool of Chemical Engineering and the Environment, Beijing Institute of Technology, 5 South Zhongguancun Street, Haidian District, Beijing 100081, P. R. of China

,

Fu-Xue Chen*

^aSchool of Chemical Engineering and the Environment, Beijing Institute of Technology, 5 South Zhongguancun Street, Haidian District, Beijing 100081, P. R. of China

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Abstract

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Abstract

An organocatalytic asymmetric sulfa-Michael addition of thiols to β-trifluoromethyl β,β-disubstituted (E)-enones in the presence of 10 mol% of a cinchona alkaloid-derived thiourea catalyst provides direct and simple access to chiral trifluoromethyl tertiary thioethers in high yields and up to 76% ee.

Key words

asymmetric catalysis - enones - Michael additions - organocatalysis - thiols - sulfides

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References

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All catalysts used in this study were identical with those in ref. 6c; see also:

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