Metal-Free Oxyaminations of Alkenes Using Hydroxamic Acids

被引：125

作者：

Schmidt, Valerie A. ^{[1
]}

Alexanian, Erik J. ^{[1
]}

机构：

[1] Univ N Carolina, Dept Chem, Chapel Hill, NC 27599 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 30期

关键词：

CATALYZED AMINOHYDROXYLATION; AMINOACETOXYLATION; HYDRAZINES; ESTERS;

D O I：

10.1021/ja204255e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A radical-mediated approach to metal-free alkene oxyamination is described. This method capitalizes on the unique reactivity of the amidoxyl radical in alkene additions to furnish a general difunctionalization using simple diisopropyl azodicarboxylate (DIAD) as a radical trap. This protocol capitalizes on the intramolecular nature of the process, providing single regioisomers in all cases. Difunctionalizations of cyclic alkenes provide trans oxyamination products inaccessible using current methods with high levels of stereoselectivity, complementing cis-selective oxyamination processes.

引用

页码：11402 / 11405

页数：4

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