Issue 86, 2013
From the journal:

Chemical Communications

Copper mediated stereoselective synthesis of C-glycosides from unactivated alkynes†‡

Anil Kumar Kusunuru,ab   Madhubabu Tatina,ab   Syed Khalid Yousuf*c  and  Debaraj Mukherjee*ab  

* Corresponding authors

a Academy of Scientific and Innovative Research, India

b CSIR-Indian Institute of Integrative Medicine, Jammu, India
E-mail: dmukherjee@iiim.ac.in
Fax: +91-011-256-9111

c Indian Institute of Integrative Medicine Br. Srinagar, India
E-mail: khalidiiim@gmail.com

Abstract

A highly stereoselective rapid C-glycosylation reaction has been developed between glycal and unactivated alkynes in the presence of coppertriflate and ascorbic acid at low catalyst loading and at room temperature. A wide variety of glycals and aryl acetylenes participate in the reaction smoothly. TfOH generated during the reduction of Cu(OTf)2 by ascorbic acid may be the active catalyst for the glycosylation.

Graphical abstract: Copper mediated stereoselective synthesis of C-glycosides from unactivated alkynes

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Article information

DOI
https://doi.org/10.1039/C3CC44250K
Article type
Communication
Submitted
05 Jun 2013
Accepted
19 Aug 2013
First published
21 Aug 2013

Chem. Commun., 2013,49, 10154-10156

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Copper mediated stereoselective synthesis of C-glycosides from unactivated alkynes

A. K. Kusunuru, M. Tatina, S. K. Yousuf and D. Mukherjee, Chem. Commun., 2013, 49, 10154 DOI: 10.1039/C3CC44250K

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