Passerini/Tsuji-Trost Strategy towards Pyrrole Derivatives

Noisette Narboni (1) , Laurent El Kaim (2, 1)

1 DCSO - Laboratoire de synthèse organique
2 ENSTA Paris - École Nationale Supérieure de Techniques Avancées

The Passerini reaction of α,β‐unsaturated aldehydes affords suitable substrates for a Tsuji–Trost reaction with NH‐enamines. The latter behave as a 1,3‐bisnucleophile, which leads to the formation of pyrrole derivatives with five points of diversity through a Tsuji–Trost/Michael addition/aromatization cascade.

Keywords: N heterocycles; homogeneous catalysis; Synthetic methods; Cyclization; Multicomponent reactions

Domains: Organic chemistry

Noisette Narboni, Laurent El Kaim. Passerini/Tsuji-Trost Strategy towards Pyrrole Derivatives. European Journal of Organic Chemistry, 2017, 2017 (29), pp.4242-4246. ⟨10.1002/ejoc.201700653⟩. ⟨hal-02094146⟩