[3+2] Cycloaddition of an Azomethyne Ylide and Vinyl Sulfonyl Fluorides ? an Approach to Pyrrolidine-3-sulfonyl Fluorides

被引：32

作者：

Mykhalchuk, Volodymyr L. ^{[1
,2
]}

Yarmolchuk, Vladimir S. ^{[1
,2
]}

Doroschuk, Roman O. ^{[1
,2
]}

Tolmachev, Andrey A. ^{[1
,2
]}

Grygorenko, Oleksandr O. ^{[1
,2
]}

机构：

[1] Enamine Ltd, Chervonotkatska St 78, UA-02094 Kiev, Ukraine

[2] Natl Taras Shevchenko Univ Kyiv, Volodymyrska St 60, UA-01601 Kiev, Ukraine

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 2018卷 / 22期

关键词：

Sulfur; Nitrogen heterocycles; Click chemistry; Cycloaddition; Azomethine ylides; ASYMMETRIC 1,3-DIPOLAR CYCLOADDITION; DIASTEREOSELECTIVE SYNTHESIS; CONFORMATIONAL BEHAVIOR; BETA; DERIVATIVES; PYRROLIDINES; PEPTIDES; PROLINE; SULTAMS; DESIGN;

D O I：

10.1002/ejoc.201800521

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[3+2] Cycloaddition reactions of vinyl sulfonyl fluorides with an in-situ generated nonstabilized azomethine ylide is described for the first time. The resulting pyrrolidine-3-sulfonyl fluorides were obtained in 50-83% yield on a scale of up to 25 g. Their utility as reagents for sulfur(VI)-fluoride exchange (SuFEx) and some other transformations was also demonstrated.

引用

页码：2870 / 2876

页数：7

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