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Catalytic Enantioselective Entry to Triflones Featuring a Quaternary Stereocenter

[Image: see text] A highly enantioselective one-pot synthesis of functionalized triflones, bearing a quaternary stereocenter, has been developed, exploiting the Michael reaction of α-(trifluoromethylsulfonyl) aryl acetic acid esters with N-acryloyl-1H-pyrazole catalyzed by commercially available Tak...

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Detalles Bibliográficos
Autores principales: Franco, Francesca, Meninno, Sara, Overgaard, Jacob, Rossi, Sergio, Benaglia, Maurizio, Lattanzi, Alessandra
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9490835/
https://www.ncbi.nlm.nih.gov/pubmed/35687515
http://dx.doi.org/10.1021/acs.orglett.2c01589
Descripción
Sumario:[Image: see text] A highly enantioselective one-pot synthesis of functionalized triflones, bearing a quaternary stereocenter, has been developed, exploiting the Michael reaction of α-(trifluoromethylsulfonyl) aryl acetic acid esters with N-acryloyl-1H-pyrazole catalyzed by commercially available Takemoto’s catalyst, followed by nucleophilic acyl substitution with alcohols. Preliminary investigations highlighted the attractive potential of the triflinate anion as the leaving group for stereocontrolled postfunctionalizations.