Substrate-Controlled Chemoselective Reactions of Isocyanoacetates with Amides and Lactams

被引：25

作者：

Zheng, Jian-Feng ^{[1
]}

Hu, Xiu-Ning ^{[1
]}

Xu, Zhen ^{[1
]}

Cai, Dong-Cheng ^{[1
]}

Shen, Tai-Long ^{[1
]}

Huang, Pei-Qiang ^{[1
]}

机构：

[1] Xiamen Univ, Fujian Prov Key Lab Chem Biol, Dept Chem,Coll Chem & Chem Engn, iChEM,Collaborat Innovat Ctr Chem Energy Mat, Xiamen 361005, Fujian, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 18期

基金：

中国国家自然科学基金;

关键词：

DIASTEREOSELECTIVE MANNICH REACTION; REDUCTIVE NUCLEOPHILIC-ADDITION; ASYMMETRIC TOTAL-SYNTHESIS; SECONDARY AMIDES; TERTIARY AMIDES; BOND FORMATION; ALPHA-ISOCYANOACETATES; MULTICOMPONENT REACTION; CATALYTIC APPLICATIONS; COUPLING REAGENTS;

D O I：

10.1021/acs.joc.7b01768

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Versatile and chemoselective C-C bond forming methods for the one-pot transformation of amides into other classes of compounds are highly demanding. In this report, we demonstrate the reductive addition of isocyanoacetates to common amides and lactams to produce 5-methoxyoxazoles or bicyclic imidazolines. This one-pot procedure involves partial reduction of amides with Schwartz reagent and chemoselective addition of the carbon of isocyanide group or alpha-carbon in isocyanoacetates. The quite different reactivity of the isocyanoacetate is due to the different steric hindrance of the amides and lactams.

引用

页码：9693 / 9703

页数：11

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