带有(2'Z)-氟乙烯基α-支链的季铵氨基酸的合成：潜在的磷酸吡哆醛（PLP）酶失活剂
Synthesis of quaternary amino acids bearing a (2'Z)-fluorovinyl alpha-branch: potential PLP enzyme inactivators.
作者信息
Berkowitz David B, de la Salud-Bea Roberto, Jahng Wan-Jin
机构信息
Department of Chemistry, University of Nebraska, Lincoln, NE 68588-0304, USA.
出版信息
Org Lett. 2004 May 27;6(11):1821-4. doi: 10.1021/ol049422u.
Abstract
Protected alpha-formyl amino acids, themselves available from the corresponding alpha-vinyl amino acids, are stereoselectively transformed into the (Z)-configured alpha-(2'-fluoro)vinyl amino acids via a three-step sequence. The route employs McCarthy's reagent, diethyl alpha-fluoro-alpha-(phenylsulfonyl)methyl phosphonate, and proceeds via the intermediate (E)-alpha-fluorovinyl sulfones and (E)-alpha-fluorovinylstannanes. The latter may either be exploited as novel cross-coupling partners for fluorovinyl branch extension or be globally deprotected, to provide the title compounds. [structure: see text]
摘要
本身可由相应的α-乙烯基氨基酸制得的受保护的α-甲酰基氨基酸，通过三步反应序列被立体选择性地转化为(Z)构型的α-(2'-氟)乙烯基氨基酸。该路线使用了麦卡锡试剂，即α-氟-α-(苯磺酰基)甲基膦酸二乙酯，并通过中间体(E)-α-氟乙烯基砜和(E)-α-氟乙烯基锡烷进行反应。后者既可以用作氟乙烯基支链延伸的新型交叉偶联伙伴，也可以进行整体脱保护，以提供标题化合物。[结构：见原文]
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