Asymmetric rhodium-catalyzed 1,4- and 1,2-additions of arylboronic acids to activated ketones in water at room temperature using a mixed sulfur-olefin ligand

Article abstract of DOI:10.1002/adsc.201201065

Performing catalytic enantioselective reactions, especially enantioselective carbon-carbon bond forming reactions, in water without using any organic solvents is one of the important goals in modern asymmetric synthesis. Herein, we report an efficient enantioselective micellar catalytic approach for the 1,4-addition of arylboronic acids to cyclic ketones. Noteworthy, applying the same catalytic system we have also developed the first addition of boronic acids to the more challenging α-keto carbonyl compounds in water, affording tertiary carbinols with high yields and high enantioselectivities. Beside the mild conditions used, the reported processes use as catalyst precursor the robust sulfinamido-olefin mixed ligand 1 obtained on a multigram scale and in one step from a sugar-derived sulfinate ester. Copyright