Issue 2, 2007
From the journal:

New Journal of Chemistry

Mechanistic study of the ring-size modulation in Michael–Dieckmann type reactions of 2-acylaminoacrylates with ketene diethyl acetal†‡

Alberto Avenoza,*a   Jesús H. Busto,a   Noelia Canal,a   José I. García,*b   Gonzalo Jiménez-Osés,a   Jesús M. Peregrinaa  and  Marta Pérez-Fernándeza  

* Corresponding authors

a Departamento de Química, Universidad de La Rioja, Grupo de Síntesis Química de La Rioja, U.A.-C.S.I.C., Spain
E-mail: alberto.avenoza@dq.unirioja.es
Fax: +34 941299655

b Departamento de Química Orgánica, Instituto de Ciencia de Materiales de Aragón, C.S.I.C.-Universidad de Zaragoza, Spain
E-mail: jig@unizar.es
Fax: +34 976762077

Abstract

An unexpected modulation of the chemoselectivity in the Michael–Dieckmann type reactions of 2-acylaminoacrylates with ketene diethyl acetal is observed, depending on the nature of the acylamino group. Experimental and theoretical studies are presented to offer insights into the origin of this substituent effect in terms of a polar stepwise mechanism.

Graphical abstract: Mechanistic study of the ring-size modulation in Michael–Dieckmann type reactions of 2-acylaminoacrylates with ketene diethyl acetal

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Article information

DOI
https://doi.org/10.1039/B615220A
Article type
Paper
Submitted
19 Oct 2006
Accepted
23 Nov 2006
First published
19 Dec 2006

New J. Chem., 2007,31, 224-229

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Mechanistic study of the ring-size modulation in Michael–Dieckmann type reactions of 2-acylaminoacrylates with ketene diethyl acetal

A. Avenoza, J. H. Busto, N. Canal, J. I. García, G. Jiménez-Osés, J. M. Peregrina and M. Pérez-Fernández, New J. Chem., 2007, 31, 224 DOI: 10.1039/B615220A

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