A direct organocatalytic entry to selectively protected aldopentoses and derivatives

被引：43

作者：

Grondal, Christoph ^{[1
]}

Enders, Dieter ^{[1
]}

机构：

[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2007年 / 349卷 / 4-5期

基金：

美国国家航空航天局;

关键词：

aldol reactions; aldopentoses; asymmetric synthesis; carbohydrates; organocatalysis;

D O I：

10.1002/adsc.200600573

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The proline-catalysed aldol reaction of 2,2dimethyl- 1,3-dioxan-5 -one with dimethoxyacetaldehyde is used as the key reaction according to the biomimetic C-3 + C-n strategy for de novo carbohydrate synthesis. Based on the Whitesides inversion strategy, protected D-erythro-pentos-4-ulose (de > 96 %, ee = 94 %) was employed for a rapid and divergent entry to various selectively and partly orthogonal protected aldopentoses and derivatives, like amino sugars, thio sugars, deoxy sugars, 4-C-substituted (alkylated) aldopentoses and epoxy sugars.

引用

页码：694 / 702

页数：9

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