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Issue 2, 2007
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Mechanistic study of the ring-size modulation in Michael–Dieckmann type reactions of 2-acylaminoacrylates with ketene diethyl acetal

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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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Publication details

The article was received on 19 Oct 2006, accepted on 23 Nov 2006 and first published on 19 Dec 2006


Article type: Paper
DOI: 10.1039/B615220A
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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