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

a   Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain
,
Alberto Ponce
a   Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain
,
Ian Maclean
a   Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain
,
Javier Adrio
a   Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain
b   Institute 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
a   Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain
b   Institute for Advanced Research in Chemical Sciences (IAdChem), Universidad Autónoma de Madrid and Centro de Innovación en Química Avanzada (ORFEO-CINQA), 28049 Madrid, Spain
› Author Affiliations
We thank the Ministerio de Ciencia e Innovación (MICINN) and Fondo Europeo de Desarrollo Regional (FEDER, UE) for financial support (Agencia Estatal de Investigación/Project PGC2018-098660-B-100). J. C. thanks the Ministerio de Educación Cultura y Deportes for a FPU fellowship. A. P. thanks the MICINN for a predoctoral fellowship.


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.

Supporting Information



Publication History

Received: 28 March 2022

Accepted after revision: 19 April 2022

Accepted Manuscript online:
19 April 2022

Article published online:
09 June 2022

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