Issue 26, 2012
From the journal:

Chemical Communications

Poly(methylhydrosiloxane)-supported chiral imidazolinones: new versatile, highly efficient and recyclable organocatalysts for stereoselective Diels–Alder cycloaddition reactions†‡

Stefania Guizzetti,a   Maurizio Benaglia*a  and  Jay S. Siegel*b  

* Corresponding authors

a Dipartimento di Chimica Organica e Industriale, Università di Milano, via Venezian 21, Milano, Italy
E-mail: Maurizio.Benaglia@unimi.it
Fax: +390250314159
Tel: +390250314171

b Organisch-Chemisches Institut, Universität Zürich, Winterthurerstrasse 190, CH-8057 Zürich, Switzerland
E-mail: jss@oci.uzh.ch
Fax: +410446356888
Tel: +410446354281

Abstract

Poly(methylhydrosiloxane) (PMHS) supported organic catalysts promoted the Diels–Alder reaction of dienes with α,β-unsaturated aldehydes, also in pure water, in yields and enantiomeric excesses comparable to those observed with the non-supported catalysts (up to 93% ee). Recycling of the catalysts was performed with no loss of enantioselectivity for at least five reaction cycles.

Graphical abstract: Poly(methylhydrosiloxane)-supported chiral imidazolinones: new versatile, highly efficient and recyclable organocatalysts for stereoselective Diels–Alder cycloaddition reactions

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Article information

DOI
https://doi.org/10.1039/C2CC17919A
Article type
Communication
Submitted
19 Dec 2011
Accepted
26 Jan 2012
First published
26 Jan 2012

Chem. Commun., 2012,48, 3188-3190

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Poly(methylhydrosiloxane)-supported chiral imidazolinones: new versatile, highly efficient and recyclable organocatalysts for stereoselective Diels–Alder cycloaddition reactions

S. Guizzetti, M. Benaglia and J. S. Siegel, Chem. Commun., 2012, 48, 3188 DOI: 10.1039/C2CC17919A

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