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.
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