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Divergent Method to trans-5-Hydroxy-6-alkynyl/alkenyl-2-piperidinones: Syntheses of (-)-Epiquinamide and (+)-Swainsonine
Alternative Title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
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
2015
Source PublicationJ. Org. Chem.
Volume80Issue:11Pages:5824-5833
AbstractAn 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.
Subtype论文
Subject Area有机化学
DOI10.1021/acs.joc.5b00803
URL查看原文
Indexed BySCI
Language英语
WOS IDWOS:000355962300047
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Document Type期刊论文
Identifierhttp://ir.sioc.ac.cn/handle/331003/39790
Collection中科院天然产物有机化学重点实验室
Corresponding AuthorWei BG(魏邦国)
Affiliation1.复旦大学
2.中科院上海有机化学研究所
Recommended Citation
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.
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