Glycolaldehyde dimer

Moreover, Kim and coworkers have shown that a-amino-butyrolactones can be synthesized by a related process employing the amino acid homoserine with an unprotected hydroxy functionality [31]. In a more recent publication by the same research group, morpholin-2-one derivatives of type 9-37 have been prepared (Scheme 9.6) [32]. Herein, glycolaldehyde dimer 9-32 acts as a bifunctional compound, which first reacts with the a-amino acids 9-33 to give the iminium ions 9-34,... 

A series of l/f-pyrrolo[2,l-r][l,4]oxazin-l-ones 196 are also the product of an LJgi multicomponent reaction between proline (and also other a-amino acids that gave the corresponding monocyclic compounds) and several isonitriles in the presence of commercially available glycolaldehyde dimer (Equation 3) <20010L4149>. 

Substituted morpholin-2-one-5-carboxamide derivatives have been efficiently synthesized from commercially available glycolaldehyde dimer as the bifunctional component with various a-amino acids and isocyanides [80]. 

Yu and co-workers32 have reported bis-THF syntheses using Lewis acid-catalyzed reaction of commercially available 2,3-dihydrofiiran (12) and glycolaldehyde dimer 25, as shown in Scheme 5. The use of Sc(OTt)3 and (S)-26 as chiral ligand in CH2C12 at 0 °C provided bis-THF alcohol 11 in a 85 15 mixture of enantiomers by GC analysis. The use of Cu[Pybox] gave similar results. 

The problems caused by the dimerization of glycolaldehyde are discussed in Section XIII (see p. 90). Instead of reacting with itself, the glycolaldehyde may form an acetal, either with the sugar or with the aglycon. These side-reactions have been thoroughly investigated by F. Smith and coworkers.630... 

The tendency of the sugar to form cyclic structures arises from the capacity of the carbonyl group to combine with neighboring hydroxyl groups. When there is no hydroxyl group in a position suitable for an intramolecular reaction to occur, an intermolecular reaction may take place. Thus, glycolaldehyde yields the dimer. 

Glycolaldehyde-Dihydroxyacetone Glycolaldehyde-Glyceraldehyde Glyceraldehyde Glyceraldehyde dimer Dihydroxyacetone Dihydroxyacetone dimer Glycerol... 

---