A Concise Stereoselective Synthesis of 2-Substituted 1-Aminocyclopropanecarboxylic Acids

✍ Scribed by Tarun K. Pradhan; Antoine Joosten; Jean-Luc Vasse; Philippe Bertus; Philippe Karoyan; Jan Szymoniak

• Publisher: John Wiley and Sons
• Year: 2009
• Tongue: English
• Weight: 199 KB
• Volume: 2009
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.200900656

✦ Synopsis

Abstract

A simple and stereoselective method for the preparation of (Z)‐2‐substituted 1‐aminocyclopropanecarboxylic acids is described. The common key step for these reaction sequences involves the stereoselective Ti‐mediated coupling of benzyloxy nitrile and homoallylic alcohol. The resulting 2‐hydroxyethyl‐substituted cyclopropylamine can be transformed shortly into various cyclopropane amino acid analogues on the gram scale, in good overall yields. Several syntheses of 2,3‐methanoamino acids, that is, ACCs derived from proteinogenic α‐amino acids or analogues, such as glutamic acid, arginine, homoarginine, and lysine derivatives are presented to exemplify the usefulness of the method. Additionally, starting from cyanoesters, spirocyclopropane γ‐amino acid analogues are available in this way. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)