Propargylation of Ugi Amide Dianion: An Entry into Pyrrolidinone and Benzoindolizidine Alkaloid Analogues

Alaa Zidan (1, 2) , Marie Cordier (3) , Abeer El-Naggar (2) , Nour Abd El-Sattar (2) , Mohamed Ali Hassan (2) , Ali Khalil Ali (2) , Laurent El Kaim (4, 1)

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

Propargylation of Ugi adducts under the addition of excess sodium hydride in DMSO leads to direct formation of pyrrolidinone enamides, which are useful precursors of iminium intermediates and may be trapped by various nucleophiles. This approach has been applied to the formation of benzoindolizidine alkaloids with high diversity via a Ugi/propargylation/Pictet-Spengler cyclization.

Domains: Organic chemistry

Alaa Zidan, Marie Cordier, Abeer El-Naggar, Nour Abd El-Sattar, Mohamed Ali Hassan, et al.. Propargylation of Ugi Amide Dianion: An Entry into Pyrrolidinone and Benzoindolizidine Alkaloid Analogues. Organic Letters, 2018, 20 (9), pp.2568-2571. ⟨10.1021/acs.orglett.8b00687⟩. ⟨hal-02094200⟩