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Enantioselective 5-exo-Fluorocyclization of Ene-Oximes

The enantioselective 5-exo-fluorocyclization of ene-oxime compounds was demonstrated under phase-transfer catalysis. Although deprotonative fluorinations competed, the chemical yields and the ee values of the desired isoxazoline products were generally moderate to good. The absolute stereochemistry...

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Detalles Bibliográficos
Autores principales: Rouno, Taiki, Niwa, Tomoki, Nishibashi, Kousuke, Yamamoto, Nobuharu, Egami, Hiromichi, Hamashima, Yoshitaka
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6804199/
https://www.ncbi.nlm.nih.gov/pubmed/31554247
http://dx.doi.org/10.3390/molecules24193464
Descripción
Sumario:The enantioselective 5-exo-fluorocyclization of ene-oxime compounds was demonstrated under phase-transfer catalysis. Although deprotonative fluorinations competed, the chemical yields and the ee values of the desired isoxazoline products were generally moderate to good. The absolute stereochemistry of the major isomer was determined to be S by comparison with the literature after transformation of the product to the corresponding iodinated isoxazoline.