文献类型：期刊文献

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

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

作者：Huang Xiangui[1];Shi Hongwei[1];Ren Jiangmeng[1];Liu Guixia[1];Tang Yun[1];Zeng Bubing[1]

机构：[1]E China Univ Sci & Technol, Sch Pharm, Shanghai Key Lab Chem Biol, Shanghai 200237, Peoples R China

年份：2012

卷号：30

期号：6

起止页码：1305

中文期刊名：Chinese Journal of Chemistry

外文期刊名：CHINESE JOURNAL OF CHEMISTRY

收录：;Scopus;WOS:【SCI-EXPANDED(收录号:WOS:000305389200019)，CCR-EXPANDED(收录号:WOS:000305389200019)】；CSCD:【CSCD2011_2012】；

基金：Financial support of this work from Shanghai Foundation of Science and Technology (No. 09JC1404200), the National '863' Project of China (No. 2007AA02Z301), '111' project and the Fundamental Research Funds for the Central University (No. WY1113007) are gratefully acknowledged.

语种：英文

中文关键词：（±）-Epibatidine;L-proline;diastereoselective;Michael addition

外文关键词：+/--Epibatidine; L-proline; diastereoselective; Michael addition

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 diastereoselectively 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.