Avery Thomas D, Greatrex Ben W, Pedersen Daniel Sejer, Taylor Dennis K, Tiekink Edward R T
Department of Chemistry, The University of Adelaide, South Australia 5005, Australia.
J Org Chem. 2008 Apr 4;73(7):2633-40. doi: 10.1021/jo7024256. Epub 2008 Mar 7.
1,2-Dioxines react with glycine-derived phosphonate nucleophiles via a multistep cascade reaction to give beta-cyclopropyl amino acid derivatives in good yield with excellent control of the cyclopropane stereocentres. The cyclopropyl ketones were oxidized to the corresponding carboxylic esters using Baeyer-Villiger conditions. Standard deprotection protocols produced a series of known beta-cyclopropyl amino acids that are selective and potent agonists or antagonists of the metabotropic glutamate receptors in excellent yields.
1,2-二氧杂环己二烯与甘氨酸衍生的膦酸酯亲核试剂通过多步级联反应，以良好的产率生成β-环丙基氨基酸衍生物，且对环丙烷立体中心具有出色的控制。使用拜耳-维利格条件将环丙基酮氧化为相应的羧酸酯。标准的脱保护方案以优异的产率制备了一系列已知的β-环丙基氨基酸，它们是代谢型谷氨酸受体的选择性强效激动剂或拮抗剂。
