Tandem regio- and diastereo-selective synthesis of halogenated C-vinyl glycosides from unactivated arylacetylenesElectronic supplementary information (ESI) available: Detailed experimental procedures and compound characterization data. See DOI: 10.1039/c3cc46914j

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 t...

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Bibliographic Details
Main Authors Tatina, Madhubabu, Kusunuru, Anil Kumar, Yousuf, Syed Khalid, Mukherjee, Debaraj
Format Journal Article
LanguageEnglish
Published 11.11.2013
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Summary: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. 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.
Bibliography:10.1039/c3cc46914j
Electronic supplementary information (ESI) available: Detailed experimental procedures and compound characterization data. See DOI
ISSN:1359-7345
1364-548X
DOI:10.1039/c3cc46914j