Enantioselective Carbene Cascade: An Effective Approach to Cyclopentadienes and Applications in Diels-Alder Reactions

被引：40

作者：

Wang, Xiangbo ^{[1
]}

Zhou, Yunfei ^{[1
]}

Qiu, Lihua ^{[1
]}

Yao, Ruwei ^{[1
]}

Zheng, Yang ^{[1
]}

Zhang, Cheng ^{[1
]}

Bao, Xiaoguang ^{[1
]}

Xu, Xinfang ^{[1
]}

机构：

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

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2016年 / 358卷 / 10期

关键词：

cascade reactions; cycloaddition; cyclopentadienes; diazo compounds; dirhodium catalysts; metal carbenes; H BOND INSERTION; 3+2 CYCLOADDITION; CATALYZED CYCLOISOMERIZATION; CYCLOPROPENES; DERIVATIVES; REARRANGEMENT; CYCLIZATION; INHIBITORS; ALKYNES;

D O I：

10.1002/adsc.201501106

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

An asymmetric carbene cascade reaction, which proceeds through carbene/alkyne metathesis and formal (3 + 2) cycloaddition and converts alkynyl-tethered enol diazoacetates to chiral bicyclic cyclopentadienes, is presented; and no catalytic asymmetric version of these carbene cascade transformations has been disclosed so far. The proton signals of the cyclopropene intermediates are observed in the mechanism study, which clearly demonstrate the reaction pathways. In addition, these products are intercepted via Diels-Alder reactions to provide bridged polycyclic structures in high yields and enantioselectivities.

引用

页码：1571 / 1576

页数：6

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