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Diastereoselective Synthesis of 2,3,4,5,6-Pentafluoroheptanes

Author(s): D. Farran, A. M. Z. Slawin, P. Kirsch, D. O'Hagan

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-NEt3 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.

Full version: Available here

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ISBN: 0022-3263
Publication Year: 2009
Periodical: Journal of Organic Chemistry
Periodical Number: 18
Volume: 74
Pages: 7168-7171
Author Address: