4.8 Article

Highly Enantioselective Synthesis of Pyrroloindolones and Pyrroloquinolinones via an N-Heterocyclic Carbene-Catalyzed Cascade Reaction

Journal

ORGANIC LETTERS
Volume 23, Issue 9, Pages 3777-3781

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c01203

Keywords

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Funding

  1. National Natural Science Foundation of China [21402037]
  2. Natural Science Foundation of Hebei Province [B2019201081, B2019201101]
  3. Project of Introduction of Overseas Personnel in Hebei Province [C20190503]
  4. Advanced Talents Incubation Program of the Hebei University [801260201299]

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This work describes the NHC-catalyzed Michael/Mannich/lactamization cascade reaction of enals with either indole-2-carboxaldehyde-derived aldimines or indole-7-carboxaldehyde-derived aldimines, allowing for the rapid assembly of optically active pyrroloindolones and pyrroloquinolinones derivatives under mild conditions with high yields, excellent enantioselectivities, and a broad substrate scope.
In this work, the NHC-catalyzed Michael/Mannich/lactamization cascade reaction of enals with either indole-2-carboxaldehyde-derived aldimines or indole-7-carboxaldehyde-derived aldimines is described. This protocol enables the rapid assembly of optically active pyrroloindolones and pyrroloquinolinones derivatives under mild conditions with high yields, excellent enantioselectivities, and a broad substrate scope.

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