Rhodium-catalyzed asymmetric arylation of β,γ-unsaturated α-ketoamides for the construction of nonracemic γ,γ- diarylcarbonyl compounds

Abstract

A highly regio- and enantioselective rhodium-catalyzed 1,4-addition of arylboronic acids to β,γ-unsaturated α-ketoamides using a simple new chiral sulfinylphosphine ligand is described. This transformation provides an attractive approach to construct chiral nonracemic γ,γ-diarylsubstituted carbonyl compounds, as exemplified in the concise syntheses of sertraline and tetrahydroquinoline-2-carboxylamide. Constructing chiral carbonyls: A simple new chiral sulfinylphosphine ligand L was developed, which promoted excellent 1,4-selectivities and enantioselectivities in the rhodium-catalyzed conjugate addition of arylboronic acids to β,γ-unsaturated α-ketoamides. The desired γ,γ-diaryl-α-ketocarbonyl compounds were afforded with high yields and high optical purities. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.