Synthesis of Diaryl α-Hydroxycarboxylic Acid Derivatives via Three-Component Reactions of o -Quinone Diimides with Alcohols and Diazo Compounds

Abstract Highly regioselective three-component reactions of o-quinone diimides with alcohols and diazo compounds have been developed with a rhodium catalyst. This transformation is proposed to proceed through a Michael-type trapping of oxonium ylide intermediates with arylation reagents, giving access to a range of diaryl α-hydroxycarboxylic acid derivatives bearing an oxa-quaternary center in good yields. This reaction featured broad substrate scope, scale-up synthesis, and late-stage functionalization of the complex molecule.