One-pot Fluorination and Organocatalytic Robinson Annulation for Asymmetric Synthesis of Mono- and Difluorinated Cyclohexenones

A one-pot fluorination and organocatalytic Robinson annulation sequence has been developed for asymmetric synthesis of 6-fluoroyclohex-2-en-1-ones and 4,6-difluorocyclohex-2-en-1-ones. The reactions promoted by cinchona alkaloid amine afforded products bearing two or three stereocenters in good to e...

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Detalles Bibliográficos
Autores principales: Huang, Xin, Zhao, Weizhao, Zhang, Xiaofeng, Liu, Miao, Vasconcelos, Stanley N. S., Zhang, Wei
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2018
Materias:
Communication
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6225330/
https://www.ncbi.nlm.nih.gov/pubmed/30181479
http://dx.doi.org/10.3390/molecules23092251
Descripción
Sumario:A one-pot fluorination and organocatalytic Robinson annulation sequence has been developed for asymmetric synthesis of 6-fluoroyclohex-2-en-1-ones and 4,6-difluorocyclohex-2-en-1-ones. The reactions promoted by cinchona alkaloid amine afforded products bearing two or three stereocenters in good to excellent yields with up to 99% ee and 20:1 dr.

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