Preparation of Fluorinated Tetrahydropyrans and Piperidines using a New Nucleophilic Fluorination Reagent DMPU/HF.
DMPU/HF (HF content 65 wt %/wt) is an ideal nucleophilic fluorination reagent for the diastereoselective synthesis of substituted 4-fluorotetrahydropyrans and 4-fluoropiperidines via a fluoro-Prins reaction. When compared to classical nucleophilic fluorination reagents like pyridine/HF, DMPU/HF gives both higher yields and better diastereoselectivity.
†Department of Chemistry, University of Louisville, Louisville, Kentucky 40292, United States.
Otome E
OE
Okoromoba
†Department of Chemistry, University of Louisville, Louisville, Kentucky 40292, United States.
Gerald B
GB
Hammond
‡College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, 2999 North Renmin Lu, Shanghai 201620, China.
Bo
B
Xu
D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D054879:Halogenation; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000475:Alkenes; D006845:Hydrocarbons, Fluorinated; D007202:Indicators and Reagents; D010880:Piperidines