Issue 97, 2013

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

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

Supplementary files

Article information

Article type
Communication
Submitted
10 Sep 2013
Accepted
12 Oct 2013
First published
14 Oct 2013

Chem. Commun., 2013,49, 11409-11411

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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