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Issue 12, 2009
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Stereoselective Reformatskii–Claisen rearrangement: synthesis of 2′,3′-dideoxy-6′,6′-difluoro-2′-thionucleosides

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Abstract

A new approach for the stereoselective synthesis of 2′,3′-dideoxy-6′,6′-difluoro-2′-thionucleosides, analogues of highly bioactive L-OddC and 3TC, has been developed viaTMSCl/pyridine induced stereoselective Reformatskii–Claisen rearrangement of secondary allyl chlorodifluoroacetate and then a regioselective Pummerer reaction to introduce bases.

Graphical abstract: Stereoselective Reformatskii–Claisen rearrangement: synthesis of 2′,3′-dideoxy-6′,6′-difluoro-2′-thionucleosides

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Publication details

The article was received on 30 Oct 2008, accepted on 24 Dec 2008 and first published on 26 Jan 2009


Article type: Communication
DOI: 10.1039/B819289H
Chem. Commun., 2009, 1505-1507

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    Stereoselective Reformatskii–Claisen rearrangement: synthesis of 2′,3′-dideoxy-6′,6′-difluoro-2′-thionucleosides

    F. Zheng, X. Zhang and F. Qing, Chem. Commun., 2009, 1505
    DOI: 10.1039/B819289H

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