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The Dihydroxyacetone Unit—A Versatile C 3 Building Block in Organic Synthesis
Author(s) -
Enders Dieter,
Voith Matthias,
Lenzen Achim
Publication year - 2005
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200400659
Subject(s) - dhap , dihydroxyacetone , dihydroxyacetone phosphate , aldol reaction , acrolein , chemistry , organic synthesis , electrophile , stereoselectivity , natural product , combinatorial chemistry , reagent , organic chemistry , catalysis , phosphate , enzyme , glycerol
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.