Issue 52, 2020
From the journal:

Chemical Communications

Regio- and diastereoselective Pd-catalyzed synthesis of C2-aryl glycosides†

Juba Ghouilem,a   Rémi Franco,a   Pascal Retailleau,b   Mouad Alami, ORCID logo a   Vincent Gandon ORCID logo *cd  and  Samir Messaoudi ORCID logo *a  

* Corresponding authors

a Universite Paris-Saclay, CNRS, BioCIS, Châtenay-Malabry, France
E-mail: samir.messaoudi@universite-paris-saclay.fr
Tel: +33 0146835887

b Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Universite Paris-Saclay, avenue de la terrasse, 91198 Gif-sur-Yvette, France

c Université Paris-Saclay, CNRS, ICMMO, Orsay Cedex, France
E-mail: vincent.gandon@universite-paris-saclay.fr

d Laboratoire de Chimie Moléculaire (LCM), CNRS UMR 9168, Ecole Polytechnique, Institut Polytechnique de Paris, route de Saclay, 91128 Palaiseau Cedex, France

Abstract

An efficient regio- and diastereoselective arylation method of readily available 2,3-glycals with various aryl iodides has been established. Using the Pd(OAc)2/AsPh3 precatalytic system, this protocol proved to be general to prepare a variety of substituted C2-aryl glycosides in good yields with complete diastereoselectivity.

Graphical abstract: Regio- and diastereoselective Pd-catalyzed synthesis of C2-aryl glycosides

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Article information

DOI
https://doi.org/10.1039/D0CC02175J
Article type
Communication
Submitted
24 Mar 2020
Accepted
21 May 2020
First published
22 May 2020

Chem. Commun., 2020,56, 7175-7178

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Regio- and diastereoselective Pd-catalyzed synthesis of C2-aryl glycosides

J. Ghouilem, R. Franco, P. Retailleau, M. Alami, V. Gandon and S. Messaoudi, Chem. Commun., 2020, 56, 7175 DOI: 10.1039/D0CC02175J

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