Reagents for Storage and Regeneration of Nonstabilized Azomethine Ylides: Spiroanthraceneoxazolidines

被引：36

作者：

Buev, Evgeny M. ^{[1
]}

Moshkin, Vladimir S. ^{[1
]}

Sosnovskikh, Vyacheslav Y. ^{[1
]}

机构：

[1] Ural Fed Univ, Inst Nat Sci, Dept Chem, Ekaterinburg 620000, Russia

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 08期

基金：

俄罗斯科学基金会;

关键词：

FLASH VACUUM THERMOLYSIS; ALPHA-AMINO-ACIDS; 1,3-DIPOLAR CYCLOADDITION; STEREOSPECIFIC SYNTHESIS; 3-SUBSTITUTED COUMARINS; DECARBOXYLATIVE ROUTE; 2-AZAALLYL ANIONS; N-OXIDE; DERIVATIVES; 5-ARYLOXAZOLIDINES;

D O I：

10.1021/acs.orglett.6b00475

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Nonstabilized azomethine ylides are easily trapped by anthraquinone to form stable spiro-oxazolidines, which have an unusual ability to undergo a cycloreversion in the presence of other dipolarophiles at 120-150 degrees C. All tested recycloadditions with carbonyl compounds and electron-poor alkenes occurred in moderate to high yields (41-92%). Moreover, increasing the reaction temperature to 210 degrees C made it possible to obtain adducts with low reactive dipolarophiles.

引用

页码：1764 / 1767

页数：4

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