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Issue 97, 2013
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Tandem regio- and diastereo-selective synthesis of halogenated C-vinyl glycosides from unactivated arylacetylenes

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Abstract

A highly regio- and diastereo-selective synthesis of halogenated C-vinyl glycosides has been achieved from glycals and unactivated aryl acetylenes in the presence of halogenated Lewis acids via a tandem glycosylation–halogenation reaction. The Lewis acid used served the dual purpose of activating the allylic acetoxy group of glycals and serving as halogen source for Markovnikov addition across the triple bond, which makes the process atom economic. The synthesized glycosyl vinyl halides have been used as precursors for various Pd catalyzed C–C cross coupling reactions.

Graphical abstract: Tandem regio- and diastereo-selective synthesis of halogenated C-vinyl glycosides from unactivated arylacetylenes

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Publication details

The article was received on 10 Sep 2013, accepted on 12 Oct 2013 and first published on 14 Oct 2013


Article type: Communication
DOI: 10.1039/C3CC46914J
Citation: Chem. Commun., 2013,49, 11409-11411
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    Tandem regio- and diastereo-selective synthesis of halogenated C-vinyl glycosides from unactivated arylacetylenes

    M. Tatina, A. K. Kusunuru, S. K. Yousuf and D. Mukherjee, Chem. Commun., 2013, 49, 11409
    DOI: 10.1039/C3CC46914J

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