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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Published inMolecules (Basel, Switzerland) Vol. 23; no. 9; p. 2251
Main Authors Huang, Xin, Zhao, Weizhao, Zhang, Xiaofeng, Liu, Miao, Vasconcelos, Stanley N S, Zhang, Wei
Format Journal Article
LanguageEnglish
Published Switzerland MDPI AG 04.09.2018
MDPI
Subjects
Absolute configuration
Acidity
Asymmetric synthesis
Asymmetry
Carbon
Catalysis
Chemical reactions
Chemistry
Chemistry, Organic - methods
Communication
Crystal structure
Cyclohexanones - chemical synthesis
Cyclohexanones - chemistry
cyclohexenone
Fluorination
Fluorine
Halogenation
Michael addition
organocatalysis
Perfluorocarbons
Pharmaceutical sciences
Phenols
Proton Magnetic Resonance Spectroscopy
Robinson annulation
Structural analysis
α-fluoro-β-keto ester
Michael addition
organocatalysis
fluorination
cyclohexenone
α-fluoro-β-keto ester
Robinson annulation
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Summary: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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules23092251