The Knoevenagel condensation of aldose sugars with β-dicarbonyl compounds produces furan derivatives having polyhydroxyalkylated alkyl side chains; this reaction is known as the Garcia Gonzalez reaction. Despite the fact that these polyhydroxyalkyl furans are interesting scaffolds for synthetic chemists to utilize in the synthesis of a variety of biologically interesting molecules, the reported approach suffers from harsh conditions. The development of a general and more efficient protocol is of considerable importance, and in this manuscript, we wish to explore the role of the NaI in enhancing the activity of CeCl3.7H2O as a useful water-tolerant Lewis acid promoter for the Garcia Gonzalez reaction. The procedure proceeds with good yields at 50 °C using our system supported on SiO2 in solvent-free conditions and represents a simple and convenient methodology for the preparation of densely functionalized molecules.

SiO2-Supported CeCl3-7H(2)O-NaI Lewis acid promoter: Investigation into the Garcia Gonzalez reaction in solvent-free conditions

GUNNELLA, Roberto;MARCANTONI, Enrico;
2007-01-01

Abstract

The Knoevenagel condensation of aldose sugars with β-dicarbonyl compounds produces furan derivatives having polyhydroxyalkylated alkyl side chains; this reaction is known as the Garcia Gonzalez reaction. Despite the fact that these polyhydroxyalkyl furans are interesting scaffolds for synthetic chemists to utilize in the synthesis of a variety of biologically interesting molecules, the reported approach suffers from harsh conditions. The development of a general and more efficient protocol is of considerable importance, and in this manuscript, we wish to explore the role of the NaI in enhancing the activity of CeCl3.7H2O as a useful water-tolerant Lewis acid promoter for the Garcia Gonzalez reaction. The procedure proceeds with good yields at 50 °C using our system supported on SiO2 in solvent-free conditions and represents a simple and convenient methodology for the preparation of densely functionalized molecules.
2007
262
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11581/113645
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