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
收藏
页码：12827 / 12833
页数：7
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