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.

Keywords: asymmetric catalysis; borylation; copper catalysis; organophosphorus compounds; phosphine boronates.