Selenide-catalyzed enantioselective synthesis of trifluoromethylthiolated tetrahydronaphthalenes by merging desymmetrization and trifluoromethylthiolation

Jie Luo, Qingxiang Cao, Xiaohui Cao () and Xiaodan Zhao ()
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Jie Luo: Sun Yat-Sen University
Qingxiang Cao: Sun Yat-Sen University
Xiaohui Cao: Sun Yat-Sen University
Xiaodan Zhao: Sun Yat-Sen University

Nature Communications, 2018, vol. 9, issue 1, 1-9

Abstract: Abstract Trifluoromethylthiolated molecules are an important class of biologically active compounds and potential drug candidates. Because of the lack of efficient synthetic methods, catalytic enantioselective construction of these molecules is rare and remains a challenge. To expand this field, we herein disclose a bifunctional selenide-catalyzed approach for the synthesis of various chiral trifluoromethylthiolated tetrahydronaphthalenes bearing an all-carbon quaternary stereocenter with gem-diaryl-tethered alkenes and alkynes by merging desymmetrization and trifluoromethylthiolation strategy. The products are obtained in high yields with excellent enantio- and diastereo-selectivities. This method can be applied to the desymmetrization and sulfenylation of diols as well. Computational studies reveal that selenide can activate the electrophilic reagent better than sulfide, confirming the higher efficiency of selenide catalysis in these reactions. On the basis of the theoretical calculations, an acid-derived anion-binding interaction is suggested to exist in the whole pathway and accounts for the observed high selectivities.

Date: 2018
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DOI: 10.1038/s41467-018-02955-0

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