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Preparation of Fluorinated Tetrahydropyrans and Piperidines using a New Nucleophilic Fluorination Reagent DMPU/HF

Otome E Okoromoba¹, Gerald B Hammond¹, Bo Xu²

¹†Department of Chemistry, University of Louisville, Louisville, Kentucky 40292, United States.

Organic Letters

|August 12, 2015

Abstract:

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.

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