Enantioselective synthesis of N-Boc-1-naphthylglycine

Abstract

A new stereoselective synthesis of enantiomerically pure 1-naphthylglycine has been developed. The source of chirality is the catalytic Sharpless epoxidation. Regioselective and stereospecific ring-opening of the corresponding epoxy alcohol is performed either with sodium azide or with benzhydrylamine as ammonia synthetic equivalents. Subsequent hydrogenation in the presence of (Boc)2O affords crystalline N-Boc-3-(1-naphthyl)propane-1,2-diol which is enantiomerically enriched up to 100% ee and oxidized to the α-amino acid.