Enantioselective N-Heterocyclic Carbene-Catalyzed Cascade Reaction for the Synthesis of Pyrroloquinolines via N-H Functionalization of Indoles

S. Mukherjee , S. Shee , Thomas Poisson (1) , Tatiana Besset (1) , A.T. Biju

1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse

Functionalization of the indole N–H bond for enantioselective synthesis of biologically important pyrroloquinoline derivatives has been reported under oxidative N-heterocyclic carbene catalysis conditions. The interception of catalytically generated chiral α,β-unsaturated acylazoliums with the indole derivatives proceeds in an aza-Michael/Michael/lactonization sequence to deliver the pyrroloquinoline derivatives in good yields, diastereoselectivities, and enantioselectivities. The simultaneous enhancement of reactivity and selectivity observed in polar aprotic solvents is noteworthy.

Domaines: Chimie

S. Mukherjee, S. Shee, Thomas Poisson, Tatiana Besset, A.T. Biju. Enantioselective N-Heterocyclic Carbene-Catalyzed Cascade Reaction for the Synthesis of Pyrroloquinolines via N-H Functionalization of Indoles. Organic Letters, 2018, 20 (22), pp.6998-7002. ⟨10.1021/acs.orglett.8b02820⟩. ⟨hal-02024520⟩