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Enantioselective addition of selenosulfonates to α,β-unsaturated ketones

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Abstract

An organo-catalyzed enantioselective addition of selenosulfonates to α,β-unsaturated ketones was developed for the first time. With a chiral squaramide as an efficient catalyst, the desired α-selenylated ketones were obtained in a good yields with high enantioselectivity up to 89% ee, and good results could be obtained on a gram scale. The products could also be efficiently transformed into useful building blocks with a propenylic stereocenter; the strategy presented in this study may find further applications in organic synthesis.

Graphical abstract: Enantioselective addition of selenosulfonates to α,β-unsaturated ketones

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Publication details

The article was received on 10 Feb 2018, accepted on 21 Mar 2018 and first published on 22 Mar 2018


Article type: Paper
DOI: 10.1039/C8OB00359A
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Enantioselective addition of selenosulfonates to α,β-unsaturated ketones

    S. Luo, N. Zhang, Z. Wang and H. Yan, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB00359A

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