Scandium cation-exchanged montmorillonite catalyzed direct C-glycosylation of a 1,3-diketone, dimedone, with unprotected sugars in aqueous solution.
The condensation of dimedone with unprotected sugars in aqueous solution in the presence of a catalytic amount of Sc(3+)-montmorillonite (Sc(3+)-mont) gave 9-hydroxyalkyl-3,3,6,6,-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-diones in good yields, while the use of Sc(OTf)(3) instead of Sc(3+)-mont gave the hydroxyalkyl-6,7-dihydrobenzofuran-4(5H)-one derivatives in good yields. Furthermore, Sc(3+)-mont could be recycled without inactivation.
Sato
Shingo
S
Department of Chemistry and Chemical Engineering, Faculty of Engineering, Yamagata University, 4-3-16 Jonan, Yonezawa-shi, Yamagata 992-8510, Japan. shingo-s@yz.yamagata-u.ac.jp
Naito
Yuzo
Y
Aoki
Kazuyori
K
D001546:Bentonite / Q000737:chemistry*; D002241:Carbohydrates / Q000737:chemistry; D002384:Catalysis; D002412:Cations / Q000737:chemistry; D003512:Cyclohexanones / Q000737:chemistry*; D006031:Glycosylation; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D012538:Scandium / Q000737:chemistry*; D012996:Solutions / Q000737:chemistry; D014867:Water / Q000737:chemistry*
D002241:Carbohydrates; D002412:Cations; D003512:Cyclohexanones; D007659:Ketones; D012996:Solutions; D014867:Water; D001546:Bentonite; C004774:dimedone; D012538:Scandium