Issue 37, 2012
From the journal:

Chemical Communications

Kinetics and mechanism of organocatalytic aza-Michael additions: direct observation of enamine intermediates†‡

Sami Lakhdar,a   Mahiuddin Baidyaa  and  Herbert Mayr*a  

* Corresponding authors

a Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstr. 5-13 (Haus F), 81377 München, Germany
E-mail: Herbert.Mayr@cup.uni-muenchen.de
Fax: +49 89 2180 77717

Abstract

The imidazoles 1a–g add to the CC-double bond of the iminium ion 2 with rate constants as predicted by the equation log k = sN(N + E). Unfavourable proton shifts from the imidazolium unit to the enamine fragment in the adduct 3 account for the failure of imidazoles to take part in iminium-activated aza-Michael additions to enals.

Graphical abstract: Kinetics and mechanism of organocatalytic aza-Michael additions: direct observation of enamine intermediates

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Article information

DOI
https://doi.org/10.1039/C2CC31224G
Article type
Communication
Submitted
17 Feb 2012
Accepted
13 Mar 2012
First published
13 Mar 2012

Chem. Commun., 2012,48, 4504-4506

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Kinetics and mechanism of organocatalytic aza-Michael additions: direct observation of enamine intermediates

S. Lakhdar, M. Baidya and H. Mayr, Chem. Commun., 2012, 48, 4504 DOI: 10.1039/C2CC31224G

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