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Issue 19, 2019
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N-Heterocyclic carbene-catalyzed diastereoselective synthesis of sulfenylated indanes via sulfa-Michael–Michael (aldol) cascade reactions

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Abstract

N-Heterocyclic carbene (NHC)-catalyzed diastereoselective synthesis of multisubstituted sulfenylated indanes has been developed. In the presence of 1 mol% NHC, various thiols underwent the sulfa-Michael–Michael cascade reaction with benzenedi(enones) efficiently to form the carbon–sulfur bond and construct sulfenylated indanes in good to excellent yields with high diastereoselectivity. In addition, the NHC-catalyzed sulfa-Michael-aldol cascade reaction between o-formyl chalcone and thiols has also been demonstrated to afford sulfenylated indanes with a free hydroxyl group in moderate yields and good diastereoselectivity.

Graphical abstract: N-Heterocyclic carbene-catalyzed diastereoselective synthesis of sulfenylated indanes via sulfa-Michael–Michael (aldol) cascade reactions

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Publication details

The article was received on 26 Jan 2019, accepted on 12 Apr 2019 and first published on 12 Apr 2019


Article type: Communication
DOI: 10.1039/C9OB00210C
Org. Biomol. Chem., 2019,17, 4700-4704

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    N-Heterocyclic carbene-catalyzed diastereoselective synthesis of sulfenylated indanes via sulfa-Michael–Michael (aldol) cascade reactions

    Z. Feng, J. Luo, Y. Zhang, G. Du and L. He, Org. Biomol. Chem., 2019, 17, 4700
    DOI: 10.1039/C9OB00210C

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