Hydrogen-Bond-Mediated Cascade Reaction Involving Chalcones: Facile Synthesis of Enantioenriched Trisubstituted Tetrahydrothiophenes

Jun-Bing Ling, Yu Su, Hai-Liang Zhu, Guan-Yu Wang and Peng-Fei Xu*

*State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, 730000, P. R. China, Email: xupflzu.edu.cn

J.-B. Ling, Y. Su, H.-L. Zhu, G.-Y. Wang, P.-F. Xu, Org. Lett., 2012, 14, 1090-1093.

DOI: 10.1021/ol2034959

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Abstract

A bifunctional squaramide catalyzes a sulfa-Michael/aldol cascade reaction between 1,4-dithiane-2,5-diol and chalcones with a low catalyst loading to yield trisubstituted tetrahydrothiophenes with three contiguous stereogenic centers in a highly stereocontrolled manner.

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Key Words

Tetrahydrothiophenes, Organocatalysis

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ID: J54-Y2012-0440