Issue 37, 2011
From the journal:

Chemical Communications

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

Tukaram M. Pimpalpalle,a   Srinivasa Rao Vidadala,b   Srinivas Hotha*b  and  Torsten Linker*a  

* Corresponding authors

a Department of Chemistry, University of Potsdam, Karl-Liebknecht-Str. 24-25, 14476 Potsdam, Germany
E-mail: linker@uni-potsdam.de
Fax: +49 331 9775076
Tel: +49 331 9775212

b Department of Chemistry, Indian Institute of Science Education & Research, Pune 411021, India
E-mail: s.hotha@iiserpune.ac.in
Fax: +91 20 25899790
Tel: +91 20 25908015

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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Article information

DOI
https://doi.org/10.1039/C1CC13425F
Article type
Communication
Submitted
09 Jun 2011
Accepted
18 Jul 2011
First published
11 Aug 2011

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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