Issue 45, 2014
From the journal:

Chemical Communications

Enantio-differentiation of O-heterocycles using a binol-derived disulfonimide as a chiral solvating agent†

A. Couffin,a   O. Thillaye du Boullay,a   M. Vedrenne,b   C. Navarro,c   B. Martin-Vaca*a  and  D. Bourissou*a  

* Corresponding authors

a LHFA, CNRS UMR 5069, University of Toulouse, 118 route de Narbonne, F-31062 Toulouse, France
E-mail: dbouriss@chimie.ups-tlse.fr, bmv@chimie.ups-tlse.fr
Fax: +33 5 6155 8204

b Institut de Chimie de Toulouse (FR 2599), 118 Route de Narbonne, 31062 Toulouse Cedex 09, France

c Lacq Research Center, Arkema, Po Box 34, 64170 Lacq, France

Abstract

The disulfonimide (R)-1 enables enantio-differentiation of a large scope of chiral O-heterocycles, thanks to the formation of diastereomeric adducts. The underlying H-bond has been investigated by NMR. (R)-1 has been used as a chiral solvating agent (CSA) to determine the stereochemical purity of D/L lactide by 1H NMR.

Graphical abstract: Enantio-differentiation of O-heterocycles using a binol-derived disulfonimide as a chiral solvating agent

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Article information

DOI
https://doi.org/10.1039/C4CC00466C
Article type
Communication
Submitted
19 Jan 2014
Accepted
16 Apr 2014
First published
16 Apr 2014

Chem. Commun., 2014,50, 5997-6000

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Enantio-differentiation of O-heterocycles using a binol-derived disulfonimide as a chiral solvating agent

A. Couffin, O. Thillaye du Boullay, M. Vedrenne, C. Navarro, B. Martin-Vaca and D. Bourissou, Chem. Commun., 2014, 50, 5997 DOI: 10.1039/C4CC00466C

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