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

Javier Corpas; Alberto Ponce; Ian Maclean; Javier Adrio; Juan C. Carretero

doi:10.1055/a-1829-0262

Synthesis, Table of Contents

Synthesis 2022; 54(21): 4673-4682
DOI: 10.1055/a-1829-0262

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

Javier Corpas

^aDepartamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain

,

Alberto Ponce

^aDepartamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain

,

Ian Maclean

^aDepartamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain

,

Javier Adrio∗

^aDepartamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain

^bInstitute for Advanced Research in Chemical Sciences (IAdChem), Universidad Autónoma de Madrid and Centro de Innovación en Química Avanzada (ORFEO-CINQA), 28049 Madrid, Spain

,

Juan C. Carretero∗

^aDepartamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain

^bInstitute for Advanced Research in Chemical Sciences (IAdChem), Universidad Autónoma de Madrid and Centro de Innovación en Química Avanzada (ORFEO-CINQA), 28049 Madrid, Spain

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Abstract

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Dedicated to Prof. Joan Bosch on the occasion of his retirement

Abstract

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.

Key words

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

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References

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Supplementary Material

Supporting Information