Rhodium-catalyzed decarbonylation of aldoses.
A catalytic procedure is described for decarbonylation of unprotected aldoses to afford alditols with one less carbon atom. The reaction is performed with the rhodium complex Rh(dppp)2Cl in a refluxing diglyme-DMA solution. A slightly improved catalyst turnover is observed when a catalytic amount of pyridine is added. Under these conditions most hexoses and pentoses undergo decarbonylation into the corresponding pentitols and tetrols in isolated yields around 70%. The reaction has been applied as the key transformation in a five-step synthesis of L-threose from D-glucose.
Monrad
Rune Nygaard
RN
Center for Sustainable and Green Chemistry, Building 201, Department of Chemistry, Technical University of Denmark, DK-2800 Lyngby, Denmark.
Madsen
Robert
R
D002248:Carbon Monoxide / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D009005:Monosaccharides / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry*; D013402:Sugar Alcohols / Q000138:chemical synthesis / Q000737:chemistry; D013997:Time Factors
D009005:Monosaccharides; D009942:Organometallic Compounds; D013402:Sugar Alcohols; D002248:Carbon Monoxide; D012238:Rhodium