4.5 Article

Catalyst-Controlled Chemodivergent [3+3] and [3+2] Formal Cycloadditions of Azomethine Ylides with Diphenylcyclopropenone

Journal

SYNTHESIS-STUTTGART
Volume 54, Issue 21, Pages 4673-4682

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/a-1829-0262

Keywords

chemodivergent reactions; [3+3] and [3+2] cycloadditions; azomethine ylide; cyclopropenone

Funding

  1. Ministerio de Ciencia e Innovacion (MICINN)
  2. Fondo Europeo de Desarrollo Regional (FEDER, UE) [PGC2018-098660-B-100]
  3. Ministerio de Educacion Cultura y Deportes
  4. MICINN

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Chemodivergent cycloadditions of azomethine ylides with diphenylcyclopropenone have been developed, involving either Cu-catalyzed [3+3] or Ag-catalyzed [3+2] processes. These reactions provide a highly efficient method for the preparation of aromatic substituted dihydropyridinones and dihydropyrrolones with excellent regio and diastereoselectivities.
Chemodivergent cycloadditions of azomethine ylides with diphenylcyclopropenone involving either Cu-catalyzed [3+3] or Ag-catalyzed [3+2] processes have been developed. These transformations provide a highly efficient method for the preparation of a variety of aromatic substituted dihydropyridinones and dihydropyrrolones with excellent regio and diasteroselectivities.

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