In situ generation of nitrilium from nitrile ylide and the subsequent Mumm rearrangement: copper-catalyzed synthesis of unsymmetrical diacylglycine esters

被引：29

作者：

Chen, Jijun ^{[1
]}

Shao, Ying ^{[1
,2
]}

Ma, Liang ^{[1
]}

Ma, Meihua ^{[1
]}

Wan, Xiaobing ^{[1
]}

机构：

[1] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Peoples R China

[2] Changzhou Univ, Adv Catalysis & Green Mfg Collaborat Innovat Ctr, Jiangsu Key Lab Adv Catalyt Mat & Technol, Changzhou 213164, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2016年 / 14卷 / 45期

基金：

中国博士后科学基金;

关键词：

CARBOXYLIC-ACIDS; MULTICOMPONENT REACTIONS; EN-ROUTE; ISONITRILES; FUNCTIONALIZATION; TRANSFORMATIONS; TRANSANNULATION; CYCLOADDITION; REACTIVITY; CHEMISTRY;

D O I：

10.1039/c6ob02037b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel in situ generation of nitrilium from a nitrile ylide and the subsequent Mumm rearrangement of carboxylic acid, nitrile, and diazo compounds gave various unsymmetrical diacylglycine esters in moderate to high yields. This copper-catalyzed cascade reaction enables one-pot generation of two C-N bonds, one C=O bond, and one C-H bond, with nitrogen as the only byproduct. The reaction has a broad functional-group tolerance, is rapid, easily scales up to the 100 mmol scale, and is insensitive to air and moisture.

引用

页码：10723 / 10732

页数：10

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