Chemistry of Aziridine Carboxylic Acids, 7. Synthesis of Ethyl (2R,3S)-N-Boc- and -N-Benzyl-3-vinylaziridine-2-carboxylates: New Potential Building Blocks for Enantiomerically Pure Unsaturated Amino Acids

✍ Scribed by Jähnisch, Klaus

• Publisher: John Wiley and Sons
• Year: 1997
• Tongue: English
• Weight: 426 KB
• Volume: 1997
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.199719970419

✦ Synopsis

Abstract

Enantiomerically pure cis‐ and trans‐1__H__‐aziridine‐carboxylic acid derivatives 2a, b and 3a, b have been prepared by asymmetric Michael‐type addition of ammonia to chiral acrylates 1a, b with high syn selectivity. The title compounds were obtained from the diols 8a, b by Corey‐Winter olefination.