Synthesis of 3-Indolylglycine Derivatives via Dinuclear Zinc Catalytic Asymmetric Friedel–Crafts Alkylation Reaction

作者：Xinwei Wang, Yuan‐Zhao Hua, Min‐Can Wang · 发表于：The Journal of Organic Chemistry · 年份：2016 · DOI：10.1021/acs.joc.6b01805 · 被引用次数：41 · 研究领域：Synthesis of Indole Derivatives、Chemical Synthesis and Analysis、Chemical Synthesis and Reactions

A direct asymmetric Friedel-Crafts (F-C) alkylation reaction between a wide range of indoles and ethyl 2-(4-methoxyphenylimino)acetate catalyzed by Trost's dinuclear complex is reported. A series of 3-indolylglycine derivatives were synthesized in enantioselectivity of up to >99% enantiomeric excess (ee) using 10 mol% catalyst loading under mild conditions. This atom economic reaction could be run on a gram scale without impacting its enantioselectivity. The absolute stereochemistry of catalytic products was determined by correlation with a known configuration compound. A possible mechanism was proposed for the asymmetric induction.