An Improved Practical Route to （±）-Epibatidine through L-Proline Catalyzed Intramolecular Michael Addition  

作　　者：黄贤贵 石洪卫 任江萌 刘桂霞 唐赟 曾步兵 

机构地区：[1]Shanghai Key Laboratory of Chemical Biologv,School of Pharmacy,East China University of Science and Tech-nology,Shanghai 200237,China

出　　处：《Chinese Journal of Chemistry》2012年第6期1305-1309,共5页中国化学（英文版）

摘　　要：This paper describes a rapid and practical synthetic route involving six-step reactions towards the diastereose- lectively synthesis of （±）-endo-Epibatidine, starting from 6-chloro-3-pyridinecarboxaldehye. The effective Henry reaction gave precursor （E）-6-（6-chloropyridin-3-yl）-5-nitrohex-5-en-2-one （3a） which could be used in the next step. Various benzoic acid derivatives were used to optimize intramolecular Michael addition of ketone to pyridinylnitroolefins to provide the key intermediate 3-（6-chloropyridin-3-yl）-4-nitrocyclohexanone （±）-7a） with high yield.This paper describes a rapid and practical synthetic route involving six-step reactions towards the diastereose- lectively synthesis of （±）-endo-Epibatidine, starting from 6-chloro-3-pyridinecarboxaldehye. The effective Henry reaction gave precursor （E）-6-（6-chloropyridin-3-yl）-5-nitrohex-5-en-2-one （3a） which could be used in the next step. Various benzoic acid derivatives were used to optimize intramolecular Michael addition of ketone to pyridinylnitroolefins to provide the key intermediate 3-（6-chloropyridin-3-yl）-4-nitrocyclohexanone （±）-7a） with high yield.

关 键 词：（±）-Epibatidine L-PROLINE DIASTEREOSELECTIVE Michael addition 

分 类 号：O629.3[理学—有机化学] O621.256.7[理学—化学]