The dihydroxyacetone unit--a versatile C(3) building block in organic synthesis.
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 alpha-substitution reactions in target-oriented syntheses. Furthermore, the related 1,3-dioxins are useful equivalents of 2-substituted acrolein derivatives.
Enders
Dieter
D
Institut für Organische Chemie, Rheinisch-Westfälische Technische Hochschule, Professor-Pirlet-Strasse 1, 52074 Aachen, Germany. enders@rwth-aachen.de
Voith
Matthias
M
Lenzen
Achim
A
D000171:Acrolein / Q000031:analogs & derivatives / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D004098:Dihydroxyacetone / Q000031:analogs & derivatives / Q000737:chemistry*; D004099:Dihydroxyacetone Phosphate / Q000737:chemistry; D004146:Dioxanes / Q000138:chemical synthesis / Q000737:chemistry; D004147:Dioxins / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry; D006835:Hydrazones / Q000737:chemistry; D015394:Molecular Structure; D009930:Organic Chemicals / Q000138:chemical synthesis* / Q000737:chemistry; D011083:Polycyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D004146:Dioxanes; D004147:Dioxins; D006571:Heterocyclic Compounds; D006835:Hydrazones; D009930:Organic Chemicals; D011083:Polycyclic Compounds; D004099:Dihydroxyacetone Phosphate; D000171:Acrolein; D004098:Dihydroxyacetone