Issue 11, 2012
From the journal:

Chemical Communications

Hexafluorobenzene: a powerful solvent for a noncovalent stereoselective organocatalytic Michael addition reaction†‡

Alessandra Lattanzi,*a   Claudia De Fusco,a   Alessio Russo,a   Albert Poaterb  and  Luigi Cavallo*ac  

* Corresponding authors

a Dipartimento di Chimica e Biologia, Via Ponte don Melillo, Fisciano, Italy
E-mail: lattanzi@unisa.it, lcavallo@unisa.it
Fax: +39 089 969603

b Catalan Institute for Water Research (ICRA), H2O Building, Scientific and Technological Park of the University of Girona, Spain

c King Abdullah University of Science and Technology, Thuwal 23955-6900, Kingdom of Saudi Arabia
E-mail: luigi.cavallo@kaust.edu.sa

Abstract

A dramatic enhancement of the diastereo- and enantioselectivity in the nitro-Michael addition reaction organocatalysed by a commercially available α,α-L-diaryl prolinol was disclosed when performing the reaction in unconventional hexafluorobenzene as a medium. DFT calculations were performed to clarify the origin of stereoselectivity and the role of C6F6.

Graphical abstract: Hexafluorobenzene: a powerful solvent for a noncovalent stereoselective organocatalytic Michael addition reaction

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Article information

DOI
https://doi.org/10.1039/C2CC17488J
Article type
Communication
Submitted
30 Nov 2011
Accepted
08 Dec 2011
First published
12 Dec 2011

Chem. Commun., 2012,48, 1650-1652

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Hexafluorobenzene: a powerful solvent for a noncovalent stereoselective organocatalytic Michael addition reaction

A. Lattanzi, C. De Fusco, A. Russo, A. Poater and L. Cavallo, Chem. Commun., 2012, 48, 1650 DOI: 10.1039/C2CC17488J

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