Issue 8, 2014

“Sulfolefin”: a mixed sulfinamido-olefin ligand in enantioselective rhodium-catalyzed addition of arylboronic acids to trifluoromethyl ketones

Abstract

Performing catalytic enantioselective carbon–carbon bond forming reactions, especially for the synthesis of tertiary carbinols, is one of the most challenging goals in modern asymmetric synthesis. Herein, we report an efficient enantioselective catalytic approach for the 1,2-addition of arylboronic acids to trifluoromethyl ketones affording tertiary trifluoromethyl-substituted alcohols with high yields and good enantioselectivities. The reported process uses as a catalyst precursor the shelf stable sulfinamido-olefin ligand 1, “sulfolefin”, obtained on a multigram scale and in one step from a sugar derived sulfinate ester.

Graphical abstract: “Sulfolefin”: a mixed sulfinamido-olefin ligand in enantioselective rhodium-catalyzed addition of arylboronic acids to trifluoromethyl ketones

Supplementary files

Article information

Article type
Communication
Submitted
16 Sep 2013
Accepted
17 Dec 2013
First published
20 Jan 2014

Org. Biomol. Chem., 2014,12, 1211-1214

Author version available

“Sulfolefin”: a mixed sulfinamido-olefin ligand in enantioselective rhodium-catalyzed addition of arylboronic acids to trifluoromethyl ketones

V. Valdivia, I. Fernández and N. Khiar, Org. Biomol. Chem., 2014, 12, 1211 DOI: 10.1039/C3OB41888J

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