β-偕二氟氨基酸衍生物及其Suzuki交叉偶联反应  

β-geminal Difluoro Amino Acid Derivatives and their Suzuki Cross-coupling Reaction

作　　者：刘剑 刘宇轩 唐石[1] LIU Jian;LIU Yuxuan;TANG Shi(College of Chemistry and Chemical Engineering,Jishou University,Jishou 416000,China)

机构地区：[1]吉首大学化学化工学院,湖南吉首416000

出　　处：《化工技术与开发》2023年第4期28-31,共4页Technology & Development of Chemical Industry

基　　金：吉首大学创新创业训练计划项目(S202010531037)。

摘　　要：本文探索了一条基于钯催化的、通过β-偕二氟氨基酸衍生物与杂环硼酸的Suzuki交叉偶联反应,制备氨基酸衍生物的合成路线。合成路线的起始原料是二苄胺和溴乙酸乙酯,经过胺醛缩合反应、亲核加成反应、羟基Appel溴化反应、heck重排、Suzuki还原交叉偶联等5个反应步骤,成功合成了2-(苄基(3-(4-(呋喃-3-基)苯基)烯丙基)氨基)-3-苯基己酸乙酯等氨基酸衍生物。该合成路线的起始原料价廉易得,合成步骤简便,具有清洁易操作、条件温和等优点,可为非天然氨基酸的合成提供参考。A palladium-catalyzed Suzuki cross-coupling reaction of difluoro amino acid derivatives with heterocyclic boric acid was studied in this paper.The starting materials in this synthesis route were dibenzylamine and ethyl bromoacetate.Ethyl 2-(benzyl(3-(4-(furan-3-yl)phenyl)allyl)amino)amino)-3-phenylhexanoic acid was successfully synthesized through five reaction steps of amine condensation reaction,nucleophilic addition reaction,hydroxyl Appel bromination reaction,heck rearrangement,and Suzuki reduction cross-coupling.The starting materials of the synthetic route were cheap and easy to obtain,the synthetic method had the advantages of simple steps,cleanliness,easy operation and mild conditions,and could provide reference for the synthesis of unnatural amino acids.

关 键 词：钯催化 Suzuki交叉偶联 氨基酸衍生物 

分 类 号：O623.624[理学—有机化学]