Elaridi Jomana, Patel Jim, Jackson W Roy, Robinson Andrea J
School of Chemistry, P.O. Box 23, Monash University, Victoria 3800, Australia.
J Org Chem. 2006 Sep 29;71(20):7538-45. doi: 10.1021/jo0606913.
A method to facilitate regioselective formation of multiple dicarba isosteres of cystine is described. A sequence of ruthenium-catalyzed cross metathesis and rhodium-catalyzed hydrogenation of nonproteinaceous allylglycine derivatives has been developed to achieve high-yielding and unambiguous formation of diaminosuberic acid derivatives. Allylglycine derivatives readily undergo ruthenium-catalyzed metathesis and hydrogenation to yield diaminosuberic acid derivatives in near quantitative yield. Under the same experimental conditions, prenylglycine was found to be inert to both Grubbs' and Wilkinson's catalyzed metathesis and hydrogenation, respectively, but was readily activated for metathesis via cross metathesis with Z-butene. Subsequent cross metathesis of the metathesis-formed crotylglycine derivative, followed by hydrogenation, yielded the second diaminosuberic acid derivative in excellent yield.
描述了一种促进区域选择性形成多个胱氨酸二碳类似物的方法。已开发出一系列钌催化的交叉复分解反应和铑催化的非蛋白质烯丙基甘氨酸衍生物的氢化反应，以实现高产率且明确地形成二氨基辛二酸衍生物。烯丙基甘氨酸衍生物易于发生钌催化的复分解反应和氢化反应，以接近定量的产率生成二氨基辛二酸衍生物。在相同的实验条件下，发现异戊烯基甘氨酸分别对格拉布催化剂和威尔金森催化剂催化的复分解反应和氢化反应呈惰性，但通过与Z-丁烯的交叉复分解反应可很容易地被激活用于复分解反应。复分解反应形成的巴豆基甘氨酸衍生物随后进行交叉复分解反应，接着进行氢化反应，以优异的产率生成第二种二氨基辛二酸衍生物。
