Synthesis of optically active alpha-hydroxycarbonyl compounds by (Salen)Mn(III)-catalyzed oxidation of silyl enol ethers and silyl ketene acetals

被引：38

作者：

Adam, W

Fell, RT

MockKnoblauch, C

SahaMoller, CR

机构：

[1] Institute of Organic Chemistry, University of Würzburg, D-97074 Würzburg, Am Hubland

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 36期

关键词：

D O I：

10.1016/0040-4039(96)01441-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Optically active alpha-hydroxy ketones and esters have been prepared by (salen)Mn(III)-catalyzed asymmetric oxidation of silyl enol ethers and silyl ketene acetals in high enantioselectivity, with ee values up to 81% for the alpha-hydroxy ketons and up to 57% for alpha-hydroxy esters. The extent of conversion and the enantioselectivity depends strongly on the type of oxygen donor, the pH of the aqueous bleach medium, the additive, and the substitution pattern at the enol functionality. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：6531 / 6534

页数：4