Synthesis of chiral lactams via asymmetric hydrogenation of α,β-unsaturated nitriles

Abstract

A highly efficient Rh-catalyzed enantioselective hydrogenation of α,β-unsaturated nitriles containing ester/amide groups has been developed. Under mild conditions, with a complex of rhodium and (S,S)-f-spiroPhos as the catalyst, a variety of α,β-unsaturated nitriles bearing an ester or amide group were successfully hydrogenated to the corresponding chiral nitriles with excellent enantioselectivities (up to 99.7% ee) and high turnover numbers (TON = 10 000). Furthermore, this catalyst system was also successfully applied to the synthesis of important chiral pharmacophore fragments, lactams, Paroxetine and amino acids.