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Isocyanide-based Multicomponent Reactions

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Front. Chem. | doi: 10.3389/fchem.2019.00020

Raising the diversity of Ugi reactions through selective alkylations and allylations of Ugi adducts

  • 1ENSTA ParisTech École Nationale Supérieure de Techniques Avancées, France
  • 2UMR7652 Laboratoire de Synthèse Organique (LSO), France
  • 3Ain Shams University, Egypt

We report here selective Tsuji-Trost type allylation of Ugi adducts using a strategy based on the enhanced nucleophilicity of amide dianions. Ugi adducts derived from aromatic aldehydes were easily allylated at their peptidyl position with allyl acetate in the presence of palladium catalysts. These substitutions were compared to more classical transition metal free allylations using allyl bromides.

Keywords: Ugi reaction, Tsuji-trost reaction, Ring closure metathesis, Piperidine, Dianion alkylation, allylation

Received: 30 Oct 2018; Accepted: 10 Jan 2019.

Edited by:

Alexander Dömling, University of Groningen, Netherlands

Reviewed by:

Javier Adrio, Autonomous University of Madrid, Spain
Thomas J. Müller, Institute of Organic and Macromolecular Chemistry, Heinrich Heine University Düsseldorf, Germany  

Copyright: © 2019 El Kaïm, Zidan, AbdEl-Sattar, El-Naggar and Ali. This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.

* Correspondence:
Prof. Laurent El Kaïm, ENSTA ParisTech École Nationale Supérieure de Techniques Avancées, Palaiseau, France,
Prof. Ali K. Ali, Ain Shams University, Cairo, 11566, Cairo, Egypt,