Organocatalytic enantioselective sulfa-Michael addition of thiocarboxylic acids to β-trifluoromethyl-α,β-unsaturated ketones for the construction of stereogenic carbon center bearing a sulfur atom and a trifluoromethyl group

An organocatalyzed asymmetric sulfa-Michael addition of thiocarboxylic acids to β-trifluoromethyl-α,β-unsaturated ketones with a chiral bifunctional amine-squaramide as the catalyst is presented. A wide range of chiral ketone compounds bearing a sulfur atom and a trifluoromethyl group at the stereog...

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Bibliographic Details
Published in:Tetrahedron 2019-04, Vol.75 (14), p.2206-2214
Main Authors: Hu, Wen-Fei, Zhao, Jian-Qiang, Chen, Xiao-Zhen, Zhou, Ming-Qiang, Zhang, Xiao-Mei, Xu, Xiao-Ying, Yuan, Wei-Cheng
Format: Article
Language:English
Subjects:
Asymmetric sulfa-Michael addition
Bifunctional catalysts
Organocatalysis
Thiocarboxylic acids
β-Trifluoromethyl-α,β-unsaturated ketones
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Summary:An organocatalyzed asymmetric sulfa-Michael addition of thiocarboxylic acids to β-trifluoromethyl-α,β-unsaturated ketones with a chiral bifunctional amine-squaramide as the catalyst is presented. A wide range of chiral ketone compounds bearing a sulfur atom and a trifluoromethyl group at the stereogenic carbon center could be obtained with excellent results (up to 99% yield, 97% ee) under mild conditions. The developed catalytic system is well-tolerated to both (E)-and (Z)-β-trifluoromethylated-α,β-unsaturated ketones. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2019.02.040