有机不对称催化合成(2R,3S)-瑞波西汀  

Organocatalytic asymmetric synthesis of(2R,3S)-reboxetine

作　　者：孔垂敏 宣宜宁 KONG Chui-min;XUAN Yi-ning(College of Pharmacy,Guangdong Pharmaceutical University,Guangzhou 510006,China)

机构地区：[1]广东药科大学药学院,广东广州510006

出　　处：《化学研究与应用》2024年第5期1163-1168,共6页Chemical Research and Application

基　　金：广东省科学技术厅项目(2017A020211027)资助。

摘　　要：本文研究了一种有机不对称催化合成(2R,3S)-瑞波西汀的方法。以肉桂醛为起始原料,通过不对称环氧化氧化-酯化反应得到手性中间体(2S,3R)-3-苯基环氧乙烷-2-羧酸甲酯,再分别通过发生酯胺交换、醚化、环化、还原等反应得到目标产物(2R,3S)-瑞波西汀。该方法原料廉价易得,反应步骤简单,总产率较高,并且产物具有优异的对映选择性。An organocatalytic asymmetric synthesis of(2R,3S)-reboxetine was developed.The chiral intermediate,methyl(2S,3R)-3-phenyloxirane-2-carboxylate,was prepared via asymmetric epoxidation and oxidative esterification reactions using cinnamaldehyde as the starting material.Then the target product,(2R,3S)-reboxetine,was obtained through ester-amine exchange,etherification,cyclization,and reduction reactions.The method had the advantages of cheap raw materials,simple reaction steps,high total yield and excellent enantioselectivity of products.

关 键 词：有机催化 不对称合成 抗抑郁药 瑞波西汀 

分 类 号：O643.3[理学—物理化学]