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Issue 37, 2011
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Lewis acid-catalyzed stereoselective lactonization and subsequent glycosidation of 2-C-malonyl carbohydrates

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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

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Publication details

The article was received on 09 Jun 2011, accepted on 18 Jul 2011 and first published on 11 Aug 2011


Article type: Communication
DOI: 10.1039/C1CC13425F
Chem. Commun., 2011,47, 10434-10436

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    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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