Issue 3, 2009
From the journal:

Organic & Biomolecular Chemistry

What is the mechanism of amine conjugate additions to pyrazole crotonate catalyzed by thiourea catalysts?†‡

Luis Simóna  and  Jonathan M. Goodman*a  

* Corresponding authors

a Unilever Centre For Molecular Science Informatics, Department of Chemistry, Lensfield Road, Cambridge, UK
E-mail: jmg11@cam.ac.uk
Fax: +44 (0)1223 763076
Tel: +44 (0)1223 336434

Abstract

Aminoindanol-derived thioureas catalyze proton transfer and do not stabilise anions in an asymmetric conjugate addition to pyrazole crotonate. Calculations show that the urea H-bonds play different roles in the preferred transition state and in the one leading to the minor enantiomer in the mechanism of hydroxy-thiourea catalyzed conjugate additions to pyrazole crotonates.

Graphical abstract: What is the mechanism of amine conjugate additions to pyrazole crotonate catalyzed by thiourea catalysts?

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Article information

DOI
https://doi.org/10.1039/B817283H
Article type
Paper
Submitted
02 Oct 2008
Accepted
27 Oct 2008
First published
03 Dec 2008

Org. Biomol. Chem., 2009,7, 483-487

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What is the mechanism of amine conjugate additions to pyrazole crotonate catalyzed by thiourea catalysts?

L. Simón and J. M. Goodman, Org. Biomol. Chem., 2009, 7, 483 DOI: 10.1039/B817283H

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