Published in
Royal Society of Chemistry, New Journal of Chemistry, 2(31), p. 224-229
DOI: 10.1039/b615220a
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Mechanistic study of the ring-size modulation in Michael-Dieckmann type reactions of 2-acylaminoacrylates with ketene diethyl acetal
Journal article published in 2007 by
Alberto Avenoza,
Jesús H. Busto 
,
Noelia Canal,
José I. García,
Gonzalo Jiménez-Osés ,
Jesús M. Peregrina ,
Marta Pérez-Fernández
,
Noelia Canal,
José I. García,
Gonzalo Jiménez-Osés ,
Jesús M. Peregrina ,
Marta Pérez-Fernández
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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.