Lewis acid catalyzed [2+2] cycloaddition of ynamides and propargyl silyl ethers: synthesis of alkylidenecyclobutenones and their reactivity in ring-opening and ring expansion

被引：20

作者：

Chen, Ling ^{[1
]}

Cao, Jian ^{[1
]}

Xu, Zheng ^{[1
]}

Zheng, Zhan-Jiang ^{[1
]}

Cui, Yu-Ming ^{[1
]}

Xu, Li-Wen ^{[1
,2
]}

机构：

[1] Hangzhou Normal Univ, Key Lab Organosilicon Chem & Mat Technol, Minist Educ, 1378 Wenyi West Rd,Sci Pk HZNU, Hangzhou 311121, Zhejiang, Peoples R China

[2] Chinese Acad Sci, State Key Lab Oxo Synth & Select Oxidat, LICP, Beijing 100864, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2016年 / 52卷 / 61期

基金：

中国国家自然科学基金;

关键词：

ORGANIC-SYNTHESIS; BOND ACTIVATION; ENE-YNAMIDES; DERIVATIVES; CYCLOBUTENONES; KETENES; BENZOCYCLOBUTENONES; CYCLOISOMERIZATIONS; BENZANNULATION; ALLENYLKETENES;

D O I：

10.1039/c6cc04648g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A family of four-membered enones, polysubstituted alkylidenecyclo-butenones, were easily prepared by a Lewis acid catalyzed [2+2] cycloaddition of ynamides and propargyl silyl ethers. This challenging regioselective [2+2] cycloaddition enables the efficient construction and conversion of four-membered enones, which provides high-value and structurally diverse products through the unexpected ring-opening and ring expansion of alkylidenecyclobutenone with Grignard reagents, organolithium, primary amines, and water.

引用

页码：9574 / 9577

页数：4

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