A General and Efficient Catalyst System for a Wacker-Type Oxidation Using TBHP as the Terminal Oxidant: Application to Classically Challenging Substrates

被引：103

作者：

Michel, Brian W. ^{[1
]}

Camelio, Andrew M. ^{[1
]}

Cornell, Candace N. ^{[1
]}

Sigman, Matthew S. ^{[1
]}

机构：

[1] Univ Utah, Dept Chem, Salt Lake City, UT 84112 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2009年 / 131卷 / 17期

基金：

美国国家卫生研究院;

关键词：

METHYL KETONES; DISCOVERY; OLEFINS;

D O I：

10.1021/ja901212h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Utilizing the rapidly synthesized Quinox ligand and commercially available aqueous TBHP, a Wacker-type oxidation has been developed, which efficiently converts the traditionally challenging substrate class of protected allylic alcohols to the corresponding acyloin products. Additionally, the catalytic system is general for several other substrate classes, converting terminal olefins to methyl ketones, with short reaction times. The system is scalable (20 mmol) and can be performed with a reduced catalyst loading of 1 mol%. Enantioenriched substrates undergo oxidation with complete retention of enantiomeric excess.

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收藏

页码：6076 / +

页数：3

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