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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