Enantioselective N-Heterocyclic Carbene-Catalyzed Cascade Reaction for the Synthesis of Pyrroloquinolines via N-H Functionalization of Indoles - Normandie Université Access content directly
Journal Articles Organic Letters Year : 2018

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

S. Mukherjee
  • Function : Author
S. Shee
  • Function : Author
A.T. Biju
  • Function : Author

Abstract

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.

Dates and versions

hal-02024520 , version 1 (19-02-2019)

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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⟩
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