Enantioselective synthesis of N-Boc-1-naphthylglycine

✍ Scribed by Eva Medina; Anton Vidal-Ferran; Albert Moyano; Miquel A. Pericàs; Antoni Riera

• Book ID: 104361160
• Publisher: Elsevier Science
• Year: 1997
• Tongue: English
• Weight: 407 KB
• Volume: 8
• Category: Article
• ISSN: 0957-4166
• DOI: 10.1016/s0957-4166(97)00137-7

✦ Synopsis

A new stereoselective synthesis of enantiomerically pure l-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)20 affords crystalline N-Boc-3-(l-naphthyl)propane-l,2-diol which is enantiomerically enriched up to 100% ee and oxidized to the cx-amino acid.