A dramatic acceleration of the enantioselective copper-catalyzed conjugate reduction of alpha,beta-unsaturated lactones, lactams, and esters is reported upon addition of alcohol additives. Good to excellent yields and enantioselectivities were realized using a catalyst generated in situ from CuCl(2).H(2)O, t-BuONa, p-tol-BINAP, and PIMHS, and this methodology was applied to the synthesis of (-)-Paroxetine.
“Catalytic Enantioselective Conjugate Reduction of Lactones and Lactams”, J. Am. Chem. Soc., 2003, 125(37), 11253-11258.