1-(1-Naphthyl)ethylamine and derivatives thereof as chiral modifiers in the enantioselective hydrogenation of ethyl pyruvate over Pt–alumina

Abstract

Catalytic quantities of (R)- or (S)-1-(1-naphthyl)ethylamine induce up to 82% e.e. in the hydrogenation of ethyl pyruvate over Pt–alumina, the actual modifier responsible for enantioselection being the secondary amine resulting from imine formation with ethyl pyruvate and subsequent reduction of the CN bond; a series of related derivatives has been prepared by reductive amination and tested as chiral modifiers.