Issue 77, 2015
From the journal:

RSC Advances

Intramolecular hydrogen bonding guides a cationic amphiphilic organocatalyst to highly stereoselective aldol reactions in water†

Ángel M. Valdivielso,a   Alba Catot,a   Ignacio Alfonso*a  and  Ciril Jimeno*a  

* Corresponding authors

a Department of Biological Chemistry and Molecular Modelling, Institute of Advanced Chemistry of Catalonia (IQAC-CSIC), c/Jordi Girona 18-26, E08034 Barcelona, Spain
E-mail: ignacio.alfonso@iqac.csic.es, ciril.jimeno@iqac.csic.es

Abstract

A novel amphiphilic guanidine organocatalyst, efficient for asymmetric aldol reactions of ketones in water at neutral pH, is disclosed. The reaction presented a clear substrate dependence depicting a free energy linear correlation with ee. Intramolecular hydrogen bonding in the acylguanidine moiety was identified as the key structural motif.

Graphical abstract: Intramolecular hydrogen bonding guides a cationic amphiphilic organocatalyst to highly stereoselective aldol reactions in water

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Article information

DOI
https://doi.org/10.1039/C5RA12135C
Article type
Communication
Submitted
23 Jun 2015
Accepted
10 Jul 2015
First published
10 Jul 2015

RSC Adv., 2015,5, 62331-62335

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Intramolecular hydrogen bonding guides a cationic amphiphilic organocatalyst to highly stereoselective aldol reactions in water

Á. M. Valdivielso, A. Catot, I. Alfonso and C. Jimeno, RSC Adv., 2015, 5, 62331 DOI: 10.1039/C5RA12135C

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