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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...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2018
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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. |
format | Online Article Text |
id | pubmed-6225330 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
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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