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学科主题: 有机化学
题名: Divergent Method to trans-5-Hydroxy-6-alkynyl/alkenyl-2-piperidinones: Syntheses of (-)-Epiquinamide and (+)-Swainsonine
其他题名: 利用发散法构建反式-5-羟基-6-烷基-H烯基-2-哌啶酮合成Epiquinamide和Swainsonine
作者: Si ZM(司长梅)1; Mao ZY(毛卓亚)1; Dong HQ(董汉清)1; Du ZT(杜振亭)1; Wei BG(魏邦国)1; Lin GQ(林国强)1
通讯作者: 魏邦国
刊名: J. Org. Chem.
发表日期: 2015
DOI: 10.1021/acs.joc.5b00803
卷: 80, 期:11, 页:5824-5833
收录类别: SCI
文章类型: 论文
英文摘要: An efficient diastereoselective approach to access trans-5-hydroxy-6-alkynyl/alkenyl-2-piperidinones has been developed through nucleophilic addition of alpha-chiral aldimines using alkynyl/alkenyl Grignard reagents. The diastereoselectivity of alkenyl in C-6 position of 2-piperidinone was controlled by alpha-alkoxy substitution, while the alkynyl was controlled by the coordination of the alpha-alkoxy substitution and stereochemistry of sulfinamide. The utility of this straightforward cascade process is demonstrated by the asymmetric synthesis of the (-)-epiquinamide and (+)-swainsonine.
语种: 英语
相关网址: 查看原文
WOS记录号: WOS:000355962300047
Citation statistics:
内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/39790
Appears in Collections:中科院天然产物有机化学重点实验室_期刊论文

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作者单位: 1.复旦大学
2.中科院上海有机化学研究所

Recommended Citation:
Si ZM,Mao ZY,Dong HQ,et al. Divergent Method to trans-5-Hydroxy-6-alkynyl/alkenyl-2-piperidinones: Syntheses of (-)-Epiquinamide and (+)-Swainsonine[J]. J. Org. Chem.,2015,80(11):5824-5833.
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