New stable anomeric hydroperoxides derived from 2-deoxysugars; enantioselective epoxidation of 2-methyl-1,4-naphthoquinone

被引：18

作者：

Kosnik, W

Stachulski, AV

Chmielewski, M

机构：

[1] Polish Acad Sci, Inst Organ Chem, PL-01224 Warsaw, Poland

[2] Univ Liverpool, Robert Robinson Labs, Dept Chem, Liverpool L69 7ZD, Merseyside, England

来源：

TETRAHEDRON-ASYMMETRY | 2005年 / 16卷 / 11期

关键词：

D O I：

10.1016/j.tetasy.2005.04.009

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

3.5-Di- or 3,4,6-tri-O-substituted-2-deoxysugars or their glycosides can be oxidized with hydrogen peroxide in the presence of an acid catalyst to the corresponding anomeric hydroperoxides, which are relatively stable, can be separated into pure anomers by column chromatography and stored in a refrigerator without visible decomposition. The hydroperoxides thus obtained were used for the enantioselective epoxidation of 2-methyl-1,4-naphthoquinone with ees in the range 28-47%. (c) 2005 Elsevier Ltd. All rights reserved.

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页码：1975 / 1981

页数：7

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