Divergent Method to trans-5-Hydroxy-6-alkynyl/alkenyl-2-piperidinones: Syntheses of (-)-Epiquinamide and (+)-Swainsonine
文献类型：期刊论文
| 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 |
| 刊名 | J. Org. Chem.
 |
| 出版日期 | 2015 |
| 卷号 | 80期号:11页码:5824-5833 |
| 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 |
| 通讯作者 | 魏邦国 |
| 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. |
| 学科主题 | 有机化学 |
| 收录类别 | SCI |
| 原文出处 | http://dx.doi.org/10.1021/acs.joc.5b00803 |
| 语种 | 英语 |
| WOS记录号 | WOS:000355962300047 |
| 源URL | [http://ir.sioc.ac.cn/handle/331003/39790]  |
| 专题 | 上海有机化学研究所_中科院天然产物有机化学重点实验室 |
| 作者单位 | 1.复旦大学 2.中科院上海有机化学研究所 |
| 推荐引用方式 GB/T 7714 | 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. |
| APA | 司长梅,毛卓亚,董汉清,杜振亭,魏邦国,&林国强.(2015).Divergent Method to trans-5-Hydroxy-6-alkynyl/alkenyl-2-piperidinones: Syntheses of (-)-Epiquinamide and (+)-Swainsonine.J. Org. Chem.,80(11),5824-5833. |
| MLA | 司长梅,et al."Divergent Method to trans-5-Hydroxy-6-alkynyl/alkenyl-2-piperidinones: Syntheses of (-)-Epiquinamide and (+)-Swainsonine".J. Org. Chem. 80.11(2015):5824-5833. |
入库方式： OAI收割
来源：上海有机化学研究所
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