Title of article :
Direct Ferrier rearrangement on unactivated glycals catalyzed by indium(III) chloride
Author/Authors :
Nagaraj، نويسنده , , Paramathevar and Ramesh، نويسنده , , Namakkal G. Ramesh، نويسنده ,
Issue Information :
هفته نامه با شماره پیاپی سال 2009
Pages :
4
From page :
3970
To page :
3973
Abstract :
Anhydrous InCl3 has been shown to efficiently catalyze the Ferrier rearrangement by a direct allylic substitution of the hydroxyl group at C-3 position of glycals to afford the corresponding 2,3-unsaturated glycosides in high yields at ambient temperature. This methodology obviates the need for protecting and/or activating the C-3 hydroxyl group of glycals. The reaction works in equal ease with both 4,6-di-O-benzyl-d-glucal and 4,6-di-O-benzyl-d-galactal. The mildness of InCl3 makes this approach compatible for glycosyl acceptors with acid labile groups. The generality of the reaction has been demonstrated with a diversity of alcohols, phenols, and sugar nucleophiles.
Keywords :
Lewis acid , Indium(III) chloride , Ferrier rearrangement , Disaccharides , glycals , glycosylation
Journal title :
Tetrahedron Letters
Serial Year :
2009
Journal title :
Tetrahedron Letters
Record number :
1864819
Link To Document :
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