Enantioselective synthesis of N-Boc-1-naphthylglycine
1997; Elsevier BV; Volume: 8; Issue: 10 Linguagem: Inglês
10.1016/s0957-4166(97)00137-7
ISSN1362-511X
AutoresEva Medina, Anton Vidal‐Ferran, Albert Moyano, Miquel À. Pericàs, Antoni Riéra,
Tópico(s)Asymmetric Synthesis and Catalysis
ResumoA 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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