Issue 25, 2013
From the journal:

Organic & Biomolecular Chemistry

Efficient catalysts for asymmetric Mannich reactions

Michał Rachwalski,*ab   Tim Leenders,a   Sylwia Kaczmarczyk,c   Piotr Kiełbasiński,c   Stanisław Leśniakb  and  Floris P. J. T. Rutjesa  

* Corresponding authors

a Radboud University Nijmegen, Institute for Molecules and Materials, Heyendaalseweg 135, 6525 AJ Nijmegen, The Netherlands
E-mail: m.rachwalski@science.ru.nl
Fax: +31 243653393
Tel: +31 243653202

b University of Łódź, Faculty of Chemistry, Department of Organic and Applied Chemistry, Tamka 12, 91-403 Łódź, Poland
E-mail: mrach14@wp.pl
Fax: +48 0426655162
Tel: +48 0426355767

c Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Department of Heteroorganic Chemistry, Sienkiewicza 112, 90-363 Łódź, Poland

Abstract

Efficient chiral catalysts for direct asymmetric three-component Mannich reactions of ketones, aldehydes and an amine (p-anisidine) have been developed. The corresponding β-amino carbonyl compounds (Mannich adducts) were obtained in good chemical yields and excellent enantio- and diastereoselectivities. The reaction conditions have been optimized by invoking ultrasonication and the influence of some structural moieties of the catalysts on the chemical yield and stereoselectivity of the Mannich products has been evaluated.

Graphical abstract: Efficient catalysts for asymmetric Mannich reactions

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Article information

DOI
https://doi.org/10.1039/C3OB40681D
Article type
Paper
Submitted
05 Apr 2013
Accepted
01 May 2013
First published
20 May 2013

Org. Biomol. Chem., 2013,11, 4207-4213

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Efficient catalysts for asymmetric Mannich reactions

M. Rachwalski, T. Leenders, S. Kaczmarczyk, P. Kiełbasiński, S. Leśniak and F. P. J. T. Rutjes, Org. Biomol. Chem., 2013, 11, 4207 DOI: 10.1039/C3OB40681D

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