Issue 37, 2011

Lewis acid-catalyzed stereoselective lactonization and subsequent glycosidation of 2-C-malonyl carbohydrates

Abstract

Gold(III) bromide is a suitable catalyst for the stereoselective cyclization of 2-C-malonyl carbohydrates to the anomeric center under retention of one ester group. Reopening of the lactones with alcohols in the presence of TMSOTf affords allyl, propargyl and benzyl glycosides with high α-selectivity.

Graphical abstract: Lewis acid-catalyzed stereoselective lactonization and subsequent glycosidation of 2-C-malonyl carbohydrates

Supplementary files

Article information

Article type
Communication
Submitted
09 jun 2011
Accepted
18 jul 2011
First published
11 ago 2011

Chem. Commun., 2011,47, 10434-10436

Lewis acid-catalyzed stereoselective lactonization and subsequent glycosidation of 2-C-malonyl carbohydrates

T. M. Pimpalpalle, S. R. Vidadala, S. Hotha and T. Linker, Chem. Commun., 2011, 47, 10434 DOI: 10.1039/C1CC13425F

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