Issue 13, 2012
From the journal:

Chemical Communications

Differentiation of diastereotopic bromine atoms in SN2 reactions of gem-dibromides†

Niels Münster,a   Klaus Harmsa  and  Ulrich Koert*a  

* Corresponding authors

a Department of Chemistry, Philipps-University of Marburg, Hans-Meerwein-Straße, 35043 Marburg, Germany
E-mail: koert@chemie.uni-marburg.de
Fax: +49 6421-2825677

Abstract

A novel directed SN2 reaction of conformationally biased gem-dibromides and an arenesulfinate anion is described. The reaction results in the diastereoselective formation of α-bromosulfones. The selectivity originates from pre-coordination of the nucleophile to a free hydroxyl group in the γ-position.

Graphical abstract: Differentiation of diastereotopic bromine atoms in SN2 reactions of gem-dibromides

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Article information

DOI
https://doi.org/10.1039/C2CC17599A
Article type
Communication
Submitted
05 Dec 2011
Accepted
19 Dec 2011
First published
20 Dec 2011

Chem. Commun., 2012,48, 1866-1867

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Differentiation of diastereotopic bromine atoms in SN2 reactions of gem-dibromides

N. Münster, K. Harms and U. Koert, Chem. Commun., 2012, 48, 1866 DOI: 10.1039/C2CC17599A

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