The dihydroxyacetone unit -: A versatile C3 building block in organic synthesis

被引：162

作者：

Enders, D ^{[1
]}

Voith, M ^{[1
]}

Lenzen, A ^{[1
]}

机构：

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

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2005年 / 44卷 / 09期

关键词：

acrolein derivatives; aldol reaction; asymmetric synthesis; biomimetic synthesis; hydrazones;

D O I：

10.1002/anie.200400659

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Nature employs dihydroxyacetone phosphate (DHAP) as the donor component in various enzyme-catalyzed aldol reactions. Probably the most significant example in this regard is photosynthesis, in which D-glucose, the most widespread natural product, is formed in just a few steps from DHAP. In recent years a number of synthetic equivalents of DHAP have been reported that deserve particular attention, as their applicability in organic synthesis is not limited to (stereoselective) aldol reactions. The power of these reagents has also been demonstrated convincingly in numerous other asymmetric electrophilic α-substitution reactions in target-oriented syntheses. Furthermore, the related 1,3-dioxins are useful equivalents of 2-substituted acrolein derivatives. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：1304 / 1325

页数：22

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