An asymmetric [3+2] cycloaddition of alkynes with oxiranes by selective C-C bond cleavage of epoxides: highly efficient synthesis of chiral furan derivatives

被引：38

作者：

Chen, Weiliang ^{[1
]}

Fu, Xuan ^{[1
]}

Lin, Lili ^{[1
]}

Yuan, Xiao ^{[1
]}

Luo, Weiwei ^{[1
]}

Feng, Juhua ^{[1
]}

Liu, Xiaohua ^{[1
]}

Feng, Xiaoming ^{[1
]}

机构：

[1] Sichuan Univ, Coll Chem, Minist Educ, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2014年 / 50卷 / 78期

基金：

中国国家自然科学基金;

关键词：

DONOR-ACCEPTOR CYCLOPROPANES; 2-DIAZO-3,6-DIKETOESTER-DERIVED CARBONYL YLIDES; ENANTIOSELECTIVE INTERMOLECULAR CYCLOADDITION; ONE-POT SYNTHESIS; DIRHODIUM(II) CARBOXYLATES; AROMATIC-ALDEHYDES; LEWIS-ACIDS; AMINOCYCLOPROPANES; TETRAHYDROFURANS; DIAZOESTERS;

D O I：

10.1039/c4cc04182h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient enantioselective [3+2] cycloaddition of alkynes with oxiranes via selective C-C bond cleavage of epoxides was developed. A number of optically active 2,5-dihydrofurans were obtained in excellent yields (up to 99%) and enantioselectivities (up to 95% ee) under mild reaction conditions. Moreover, chiral tetrahydrofuran could also be obtained by cycloaddition of alkene and oxirane or hydrogenation of chiral 2,5-dihydrofuran.

引用

页码：11480 / 11483

页数：4

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