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

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 sulfa-Michael-Michael cascade reaction with benzenedi(enones) efficiently to form carbon-sulfur bond and construct sulfenylated indanes in good to excellent yields with high diastereoselectivity. In addition, 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.

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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
Citation: Org. Biomol. Chem., 2019, Accepted Manuscript

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

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

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