Issue 10, 2008
From the journal:

Chemical Communications

Stereospecific debenzylative cycloetherification of carbohydrate-derived allylic alcohols, ethers and esters to form vinylC-furanosides†

Riccardo Cribiùa  and  Ian Cumpstey*a  

* Corresponding authors

a Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden
E-mail: cumpstey@organ.su.se
Fax: +46 (0)8 154908
Tel: +46 (0)8 674 7263

Abstract

Benzyl ether protected polyhydroxylated alkene compounds containing allylic alcohol, ether or ester functionality undergo a stereospecific cyclisation reaction upon treatment with TFA–acetonitrile–toluene with inversion of configuration at the allylic position and loss of a benzyl ether to give tetrahydrofurans.

Graphical abstract: Stereospecific debenzylative cycloetherification of carbohydrate-derived allylic alcohols, ethers and esters to form vinyl C-furanosides

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Article information

DOI
https://doi.org/10.1039/B718060H
Article type
Communication
Submitted
22 Nov 2007
Accepted
28 Jan 2008
First published
07 Feb 2008

Chem. Commun., 2008, 1246-1248

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Stereospecific debenzylative cycloetherification of carbohydrate-derived allylic alcohols, ethers and esters to form vinyl C-furanosides

R. Cribiù and I. Cumpstey, Chem. Commun., 2008, 1246 DOI: 10.1039/B718060H

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