Diastereoselective synthesis of 2,3,4,5,6-pentafluoroheptanes.
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.
Farran
Daniel
D
School of Chemistry and Centre for Biomolecular Sciences, University of St. Andrews, North Haugh, St. Andrews KY16 9ST, United Kingdom.
Slawin
Alexandra M Z
AM
Kirsch
Peer
P
O'Hagan
David
D
D000438:Alcohols / Q000737:chemistry; D018360:Crystallography, X-Ray; D004852:Epoxy Compounds / Q000737:chemistry; D005461:Fluorine / Q000737:chemistry; D006536:Heptanes / Q000138:chemical synthesis* / Q000737:chemistry; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D008956:Models, Chemical; D013237:Stereoisomerism
D000438:Alcohols; D004852:Epoxy Compounds; D006536:Heptanes; D006845:Hydrocarbons, Fluorinated; D005461:Fluorine