A simple and efficient diastereoselective Strecker synthesis of optically pure α-arylglycines

✍ Scribed by Rajesh H. Dave; Bhaskar D. Hosangadi

• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 830 KB
• Volume: 55
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(99)00673-0

✦ Synopsis

A simple and economical method for the synthesis of highly functionalised ct-amino nitriles, precursors to ct-arylglycines with high optical purity is reported. For this purpose, (R) or (S)-2-amino-2-phenylethanol were used as chiral auxiliaries in a 1,3 Strecker reaction. Reactions were studied with a broad range of reagent systems for the generation of cyano nucleophile. Methodology has been extended for the synthesis of (S)-~t-(2-iodo-5-nitrophenyl)glycine, (S)-~-(4-methoxypbenyi)glycine and (R)-13-(4-methoxyphenyl)alanine.