Issue 2, 2007

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

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

Supplementary files

Article information

Article type
Paper
Submitted
19 Oct 2006
Accepted
23 Nov 2006
First published
19 Dec 2006

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

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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