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

被引：8

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

来源：

CHINESE JOURNAL OF CHEMISTRY | 2012年 / 30卷 / 06期

关键词：

+/--Epibatidine; L-proline; diastereoselective; Michael addition; ASYMMETRIC-SYNTHESIS; BIFUNCTIONAL THIOUREA; CONJUGATE ADDITION; (+)-EPIBATIDINE; EPIBATIDINE; KETONES; EFFICIENT; NITROALKENE; ALDEHYDES;

D O I：

10.1002/cjoc.201200298

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：1305 / 1309

页数：5

共 40 条

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