HIGHLY EFFICIENT HYDROXYLATION OF CARBONYL-COMPOUNDS WITH DIMETHYLDIOXIRANE

被引：59

作者：

ADAM, W

PRECHTL, F

机构：

[1] Institut für Organische Chemie, Universität Würzburg, Würzburg, W-8700, Am Hubland

来源：

CHEMISCHE BERICHTE | 1991年 / 124卷 / 10期

关键词：

DIMETHYLDIOXIRANE; ENOLATES; HYDROXYLATION; ALPHA-HYDROXY CARBONYL COMPOUNDS; ENOL SILYL ETHERS;

D O I：

10.1002/cber.19911241034

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The enolates and/or enols of ketones, esters, beta-diketones, beta-oxo esters, and beta-oxo lactones were transformed by dimethyldioxirane (isolated in acetone solution or generated in situ) into their alpha-hydroxy compounds in good to excellent yields. The direct hydroxylation of the enols was significantly enhanced by the use of fluoride ion. For the enolate of camphor the exo/endo diastereoselectivity depended significantly on the metal ligand; the highest exo/endo ratio (93:7) was observed for the enol trimethylsilyl ether of camphor.

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页码：2369 / 2372

页数：4

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