Nonstabilized Azomethine Ylides in the Mannich Reaction: Synthesis of 3,3-Disubstituted Pyrrolidines, Including Oxindole Alkaloids

被引：30

作者：

Buev, Evgeny M. ^{[1
]}

Moshkin, Vladimir S. ^{[1
]}

Sosnovskikh, Vyacheslav Y. ^{[1
]}

机构：

[1] Ural Fed Univ, Inst Nat Sci & Math, Ekaterinburg 620000, Russia

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 23期

基金：

俄罗斯科学基金会;

关键词：

ALPHA-AMINO-ACIDS; C-H FUNCTIONALIZATION; ONE-POT SYNTHESIS; DECARBOXYLATIVE ROUTE; AROMATIC-ALDEHYDES; 5-ARYLOXAZOLIDINES; CYCLOADDITIONS; (+/-)-COERULESCINE; (-)-HORSFILINE; INTERMEDIATE;

D O I：

10.1021/acs.joc.7b02193

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Active methylene compounds react with in situ generated nonstabilized azomethine ylides via the domino Mannich reaction-dipolar cycloaddition to form 3,3-disubstituted pyrrolidines, including oxindole alkaloids. When the starting material possesses a single activated hydrogen, the reaction terminates at the Mannich base stage. The developed methodology was applied to a short and efficient synthesis of (+/-)-horsfiline and N-protected (+/-)-coerulescine.

引用

页码：12827 / 12833

页数：7

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