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 give...

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Bibliographic Details
Published in:Organic letters 2015-08, Vol.17 (16), p.3975-3977
Main Authors: Okoromoba, Otome E, Hammond, Gerald B, Xu, Bo
Format: Article
Language:English
Subjects:
Alkenes - chemistry
Catalysis
Cyclization
Halogenation
Hydrocarbons, Fluorinated - chemical synthesis
Hydrocarbons, Fluorinated - chemistry
Indicators and Reagents
Molecular Structure
Piperidines - chemical synthesis
Piperidines - chemistry
Stereoisomerism
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b01919