Mechanistic Study of the Ring-Size Modulation in Michael-Dieckmann type Reactions of 2-Acylaminoacrylates with Ketene Diethyl Acetal

  1. Avenoza, A. 1
  2. Busto, J.H. 1
  3. Canal, N. 1
  4. García, J.I. 2
  5. Jiménez-Osés, G. 1
  6. Peregrina, J.M. 1
  7. Pérez-Fernández, M. 1
  1. 1 Universidad de La Rioja
    info

    Universidad de La Rioja

    Logroño, España

    ROR https://ror.org/0553yr311

  2. 2 Instituto de Nanociencia y Materiales de Aragón
    info

    Instituto de Nanociencia y Materiales de Aragón

    Zaragoza, España

    ROR https://ror.org/031n2c920

Revista:
New Journal of Chemistry

ISSN: 1144-0546

Any de publicació: 2007

Volum: 31

Número: 2

Pàgines: 224-229

Tipus: Article

DOI: 10.1039/B615220A SCOPUS: 2-s2.0-33846888252 WoS: WOS:000244063100007 GOOGLE SCHOLAR lock_openDigital CSIC editor

Altres publicacions en: New Journal of Chemistry

Repositori institucional: lock_openAccés obert Editor

Resum

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. © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.