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Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyl(tropone)iron
Published on: August 12, 2019
Diastereoselective synthesis of 2,3,4,5,6-pentafluoroheptanes
Daniel Farran1, Alexandra M Z Slawin, Peer Kirsch
1School of Chemistry and Centre for Biomolecular Sciences, University of St. Andrews, North Haugh, St. Andrews KY16 9ST, United Kingdom.
Abstract:
A stereocontrolled synthesis of alkanes containing five contiguous fluorine atoms is presented. The compounds were prepared by sequential fluorination of diastereoisomeric alcohol-diepoxides. The chemistry involved epoxide ring-opening with HF.NEt(3) and deshydroxyfluorination reactions of free alcohols with Deoxo-Fluor. The fluorination reactions were all highly stereospecific, with all five fluorines being incorporated in three sequential steps. Three different diastereoisomers of the 2,3,4,5,6-pentafluoroheptyl motif were prepared as heptane-1,7-diol derivatives, a structural format amenable for incorporation of the vicinal pentafluoro scaffold into larger molecular architectures.
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