Issue 16, 2018

Enantioselective addition of selenosulfonates to α,β-unsaturated ketones

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

Supplementary files

Article information

Article type
Paper
Submitted
10 Feb 2018
Accepted
21 Mar 2018
First published
22 Mar 2018

Org. Biomol. Chem., 2018,16, 2893-2901

Enantioselective addition of selenosulfonates to α,β-unsaturated ketones

S. Luo, N. Zhang, Z. Wang and H. Yan, Org. Biomol. Chem., 2018, 16, 2893 DOI: 10.1039/C8OB00359A

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