Ruthenium-catalyzed stereospecific benzylic alkylation of optically active benzyl esters with malonate nucleophiles

Abstract

The transition metal-catalyzed stereospecific benzylic alkylation of optically active benzyl esters with active methylene compounds remains extremely rare. Herein, we describe the study for the ruthenium-catalyzed benzylic alkylation of chiral benzyl esters with malonates as a carbon nucleophile. A combination of [Cp*RuCl2]2 and picolinic acid found to be effective for the title reaction, providing the chiral benzylic alkylation products with retention of stereochemistry of the starting material. We proposed that the ruthenium catalysis would proceed via a double inversion mechanism.