A novel spirocyclic scaffold accessed via tandem Claisen rearrangement/intramolecular oxa-Michael addition

A straightforward access to novel spiro[benzofuran-2,3'-pyrrolidine]-2',5'-diones based on the Rh(2)(esp)(2)-catalyzed insertion of carbenes derived from diazo arylidene succinimides (DAS) into the O–H bond of phenols is described. The initial adducts underwent a thermally promoted Cl...

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Detalles Bibliográficos
Autores principales: Vepreva, Anastasia, Yanovich, Alexander, Dar’in, Dmitry, Kantin, Grigory, Bunev, Alexander, Krasavin, Mikhail
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2022
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9749547/
https://www.ncbi.nlm.nih.gov/pubmed/36570564
http://dx.doi.org/10.3762/bjoc.18.177
Descripción
Sumario:A straightforward access to novel spiro[benzofuran-2,3'-pyrrolidine]-2',5'-diones based on the Rh(2)(esp)(2)-catalyzed insertion of carbenes derived from diazo arylidene succinimides (DAS) into the O–H bond of phenols is described. The initial adducts underwent a thermally promoted Claisen rearrangement followed by DABCO-catalyzed intramolecular 5-exo-trig oxa-Michael addition.

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