Raising the Diversity of Ugi Reactions Through Selective Alkylations and Allylations of Ugi Adducts

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...

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Detalles Bibliográficos
Autores principales: Zidan, Alaa, El-Naggar, Abeer M., Abd El-Sattar, Nour E. A., Ali, Ali Khalil, El Kaïm, Laurent
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Frontiers Media S.A. 2019
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6361783/
https://www.ncbi.nlm.nih.gov/pubmed/30761290
http://dx.doi.org/10.3389/fchem.2019.00020
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author Zidan, Alaa
El-Naggar, Abeer M.
Abd El-Sattar, Nour E. A.
Ali, Ali Khalil
El Kaïm, Laurent
author_facet Zidan, Alaa
El-Naggar, Abeer M.
Abd El-Sattar, Nour E. A.
Ali, Ali Khalil
El Kaïm, Laurent
author_sort Zidan, Alaa
collection PubMed
description 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.
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spelling pubmed-63617832019-02-13 Raising the Diversity of Ugi Reactions Through Selective Alkylations and Allylations of Ugi Adducts Zidan, Alaa El-Naggar, Abeer M. Abd El-Sattar, Nour E. A. Ali, Ali Khalil El Kaïm, Laurent Front Chem Chemistry 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. Frontiers Media S.A. 2019-01-29 /pmc/articles/PMC6361783/ /pubmed/30761290 http://dx.doi.org/10.3389/fchem.2019.00020 Text en Copyright © 2019 Zidan, El-Naggar, Abd El-Sattar, Ali and El Kaïm. http://creativecommons.org/licenses/by/4.0/ 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.
spellingShingle Chemistry
Zidan, Alaa
El-Naggar, Abeer M.
Abd El-Sattar, Nour E. A.
Ali, Ali Khalil
El Kaïm, Laurent
Raising the Diversity of Ugi Reactions Through Selective Alkylations and Allylations of Ugi Adducts
title Raising the Diversity of Ugi Reactions Through Selective Alkylations and Allylations of Ugi Adducts
title_full Raising the Diversity of Ugi Reactions Through Selective Alkylations and Allylations of Ugi Adducts
title_fullStr Raising the Diversity of Ugi Reactions Through Selective Alkylations and Allylations of Ugi Adducts
title_full_unstemmed Raising the Diversity of Ugi Reactions Through Selective Alkylations and Allylations of Ugi Adducts
title_short Raising the Diversity of Ugi Reactions Through Selective Alkylations and Allylations of Ugi Adducts
title_sort raising the diversity of ugi reactions through selective alkylations and allylations of ugi adducts
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6361783/
https://www.ncbi.nlm.nih.gov/pubmed/30761290
http://dx.doi.org/10.3389/fchem.2019.00020
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