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Synthesis of gem-Difluorinated Oxa/Azaspiro[2.4]heptanes via Palladium-Catalyzed Spirocyclopropanation.
Yang, Linhui; Tao, Zhu; Xu, Hua-Dong; Shen, Mei-Hua; Chu, Haoke.
Afiliação
  • Yang L; School of Pharmacy, Changzhou University, Changzhou, Jiangsu 213164, China.
  • Tao Z; School of Pharmacy, Changzhou University, Changzhou, Jiangsu 213164, China.
  • Xu HD; School of Pharmacy, Changzhou University, Changzhou, Jiangsu 213164, China.
  • Shen MH; School of Pharmacy, Changzhou University, Changzhou, Jiangsu 213164, China.
  • Chu H; School of Pharmacy, Changzhou University, Changzhou, Jiangsu 213164, China.
Org Lett ; 26(27): 5782-5787, 2024 Jul 12.
Article em En | MEDLINE | ID: mdl-38940384
ABSTRACT
A palladium-catalyzed spirocyclopropanation of gem-difluoroalkenes with π-allylpalladium 1,4-dipoles has been successfully developed, which gives a powerful and straightforward synthetic strategy for the construction of novel gem-difluorinated spirocyclic compounds, 6,6-difluoro-5-oxa/azaspiro[2.4]heptanes. The scope of gem-difluoroalkenes can be extended to styrenes, acrylic esters, and acrylamides to realize the installment of various functional groups and different heteroatoms on the spirocyclic skeletons, which could be converted to valuable compounds with potential biological activity. The mechanistic investigations revealed the competition between spirocyclopropanation and ß-F elimination of π-allylpalladium zwitterionic intermediates.

Texto completo: 1 Base de dados: MEDLINE Idioma: En Ano de publicação: 2024 Tipo de documento: Article

Texto completo: 1 Base de dados: MEDLINE Idioma: En Ano de publicação: 2024 Tipo de documento: Article