A Passerini/Tsuji-Trost access to dienamide derivatives

Sihem Dali Youcef (1, 2) , Mansour Dolé Kerim (1) , Hocine Ilitki (2) , Laurent El Kaim (3, 1)

1 DCSO - Laboratoire de synthèse organique
2 USTO MB - Université des sciences et de la Technologie d'Oran Mohamed Boudiaf [Oran]
3 ENSTA Paris - École Nationale Supérieure de Techniques Avancées

The Passerini reaction of α, β-unsaturated aldehydes affords allylic acetates which may be involved in Tsuji-Trost elimations towards conjugated dienamides. The interest of these 2,4-dienamides has been demonstrated in several TiCl4 triggered Diels-Alder reactions with N-phenylmaleimide.

Keywords: Passerini; Tsuji-Trost; 1.3-Diene; Diels-Alder; Isocyanide

Domains: Organic chemistry

Sihem Dali Youcef, Mansour Dolé Kerim, Hocine Ilitki, Laurent El Kaim. A Passerini/Tsuji-Trost access to dienamide derivatives. Tetrahedron Letters, 2019, 60 (2), pp.102-105. ⟨10.1016/j.tetlet.2018.11.068⟩. ⟨hal-02096732⟩