Organic Letters 2012-02-17

Hydrogen-bond-mediated cascade reaction involving chalcones: facile synthesis of enantioenriched trisubstituted tetrahydrothiophenes.

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

Index: Org. Lett. 14(4) , 1090-3, (2012)

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Abstract

A bifunctional squaramide catalyzed sulfa-Michael/aldol cascade reaction between 1,4-dithiane-2,5-diol and chalcones with a low catalyst loading has been developed. Trisubstituted tetrahydrothiophenes with three contiguous stereogenic centers are obtained in a highly stereocontrolled manner. Additionally, a remarkable temperature effect on reaction efficiency was observed and a synthetically potential gram-synthesis was also conducted.