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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:
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
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author Huang, Xin
Zhao, Weizhao
Zhang, Xiaofeng
Liu, Miao
Vasconcelos, Stanley N. S.
Zhang, Wei
author_facet Huang, Xin
Zhao, Weizhao
Zhang, Xiaofeng
Liu, Miao
Vasconcelos, Stanley N. S.
Zhang, Wei
author_sort Huang, Xin
collection PubMed
description 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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spelling pubmed-62253302018-11-13 One-pot Fluorination and Organocatalytic Robinson Annulation for Asymmetric Synthesis of Mono- and Difluorinated Cyclohexenones Huang, Xin Zhao, Weizhao Zhang, Xiaofeng Liu, Miao Vasconcelos, Stanley N. S. Zhang, Wei Molecules Communication 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. MDPI 2018-09-04 /pmc/articles/PMC6225330/ /pubmed/30181479 http://dx.doi.org/10.3390/molecules23092251 Text en © 2018 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Communication
Huang, Xin
Zhao, Weizhao
Zhang, Xiaofeng
Liu, Miao
Vasconcelos, Stanley N. S.
Zhang, Wei
One-pot Fluorination and Organocatalytic Robinson Annulation for Asymmetric Synthesis of Mono- and Difluorinated Cyclohexenones
title One-pot Fluorination and Organocatalytic Robinson Annulation for Asymmetric Synthesis of Mono- and Difluorinated Cyclohexenones
title_full One-pot Fluorination and Organocatalytic Robinson Annulation for Asymmetric Synthesis of Mono- and Difluorinated Cyclohexenones
title_fullStr One-pot Fluorination and Organocatalytic Robinson Annulation for Asymmetric Synthesis of Mono- and Difluorinated Cyclohexenones
title_full_unstemmed One-pot Fluorination and Organocatalytic Robinson Annulation for Asymmetric Synthesis of Mono- and Difluorinated Cyclohexenones
title_short One-pot Fluorination and Organocatalytic Robinson Annulation for Asymmetric Synthesis of Mono- and Difluorinated Cyclohexenones
title_sort one-pot fluorination and organocatalytic robinson annulation for asymmetric synthesis of mono- and difluorinated cyclohexenones
topic Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6225330/
https://www.ncbi.nlm.nih.gov/pubmed/30181479
http://dx.doi.org/10.3390/molecules23092251
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