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

作者：Pradhan Tarun K; Joosten Antoine; Vasse Jean Luc; Bertus Philippe; Karoyan Philippe; Szymoniak Jan^*

来源：European Journal of Organic Chemistry, 2009, 2009(29): 5072-5078.

DOI：10.1002/ejoc.200900656

• Amino acids
• Peptidomimetics
• Diastereoselectivity
• Small ring systems
• Titanium

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 alpha-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 gamma-amino acid analogues are available in this way.

• 出版日期2009-10