Catalytic Asymmetric Synthesis of Phosphine Boronates

Abstract

The first catalytic enantioselective synthesis of ambiphilic phosphine boronate esters is presented. The asymmetric boration of α,β-unsaturated phosphine oxides catalyzed by a copper bisphosphine complex affords optically active organoboronate esters that bear a vicinal phosphine oxide group in good yields and high enantiomeric excess. The synthetic utility of the products is demonstrated through stereospecific transformations into multifunctional optically active compounds. Ambiphilic phosphine boronate esters are obtained by the asymmetric boration of α,β-unsaturated phosphine oxides with a copper/bisphosphine catalyst in good yields and high enantioselectivity. The synthetic utility of the products is demonstrated through stereospecific transformations into multifunctional optically active compounds.