4.7 Article

Diastereoselective Intramolecular [3+2]-Annulation of Donor-Acceptor Cyclopropane with Imine-Assembling Hexahydropyrrolo[3,2-c]quinolinone Scaffolds

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 81, Issue 22, Pages 11185-11194

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b02172

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Funding

  1. National Natural Science Foundation of China [21276282, 21576296]
  2. Open-End Fund for the Valuable and Precision Instruments of Central South University

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An intramolecular [3 + 2]-annulation of amide-linked donor-acceptor cyclopropane with in situ-generated imine is described. As a result, diverse hexahydropyrrolo[3,2-c]quinolinones, as the tricyclic core of martinellines, were efficiently assembled in good to excellent yield (up to 93%) with a good diastereomeric ratio (up to 98:2).

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