Issue 3, 2013
From the journal:

Green Chemistry

Organocatalytic solvent-free hydrogen bonding-mediated asymmetric Michael additions under ball milling conditions†

Manuel Jörres,a   Stefanie Mersmann,a   Gerhard Raabea  and  Carsten Bolm*a  

* Corresponding authors

a Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, D-52074 Aachen, Germany
E-mail: carsten.bolm@oc.rwth-aachen.de
Fax: +49 241 80 92 391
Tel: +49 24 80 94 675

Abstract

An efficient, solvent-free protocol for asymmetric Michael additions of α-nitrocyclohexanone to nitroalkenes using thiourea derivatives as hydrogen bonding catalysts has been developed. By performing the organocatalytic reactions in a planetary ball mill, high yields (up to 97%) and excellent enantioselectivities (er up to 98 : 2) were achieved in short reaction times with low catalyst loadings.

Graphical abstract: Organocatalytic solvent-free hydrogen bonding-mediated asymmetric Michael additions under ball milling conditions

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Article information

DOI
https://doi.org/10.1039/C2GC36906K
Article type
Communication
Submitted
28 Nov 2012
Accepted
02 Jan 2013
First published
03 Jan 2013

Green Chem., 2013,15, 612-616

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Organocatalytic solvent-free hydrogen bonding-mediated asymmetric Michael additions under ball milling conditions

M. Jörres, S. Mersmann, G. Raabe and C. Bolm, Green Chem., 2013, 15, 612 DOI: 10.1039/C2GC36906K

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