Two-step formal [3+2] cycloaddition of enones/enals and allenyl MOM ether: Gold-catalyzed highly diastereoselective synthesis of cyclopentanone enol ether containing an all-carbon quaternary center

被引：116

作者：

Huang, Xiaogen ^{[1
]}

Zhang, Liming ^{[1
]}

机构：

[1] Univ Nevada, Dept Chem 216, Reno, NV 89557 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2007年 / 129卷 / 20期

关键词：

D O I：

10.1021/ja0717717

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A two-step, highly diastereoselective formal [3+2] cycloaddition between allenyl MOM ether and an enal/enone is developed. Au activation of allenyl ethers is proposed to yield all-carbon 1,3-dipoles, which can undergo concerted intramolecular 1,3-dipolar cycloadditions. Synthetically useful cyclopentanone enol ethers containing an all-carbon quaternary center can be readily prepared with excellent diastereocontrol.

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页码：6398 / +

页数：3

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