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

Alaa Zidan (1, 2, 3) , Abeer El-Naggar (3) , Nour Abd El-Sattar (3) , Ali Khalil Ali (3) , Laurent El Kaim (1, 2)

1 ENSTA Paris - École Nationale Supérieure de Techniques Avancées
2 DCSO - Laboratoire de synthèse organique
3 Faculty of Science [ASU]

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: Tsuji-Trost reaction; Ugi reaction; allylation; metathesis; palladium; piperidines

Domains: Organic chemistry

Alaa Zidan, Abeer El-Naggar, Nour Abd El-Sattar, Ali Khalil Ali, Laurent El Kaim. Raising the Diversity of Ugi Reactions Through Selective Alkylations and Allylations of Ugi Adducts. Frontiers in Chemistry, 2019, 7 (20), ⟨10.3389/fchem.2019.00020⟩. ⟨hal-02096847⟩