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

Daniel Farran; Alexandra M. Z. Slawin; Peer Kirsch; David O'Hagan

doi:10.1021/jo901360e

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

Daniel Farran, Alexandra M. Z. Slawin, Peer Kirsch, David O'Hagan

Research output: Contribution to journal › Article › peer-review

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-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.

Original language	English
Pages (from-to)	7168-7171
Number of pages	4
Journal	The Journal of Organic Chemistry
Volume	74
Issue number	18
DOIs	https://doi.org/10.1021/jo901360e
Publication status	Published - 18 Sept 2009

Keywords

MEDICINAL CHEMISTRY
FLUORINE

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10.1021/jo901360e

Synthesis and properties of novel sequen: Synthesis and properties of novel sequentially fluorinated motifs in organcic chemistry
O'Hagan, D. (PI)
EPSRC
24/03/08 → 23/03/11
Project: Standard

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title = "Diastereoselective Synthesis of 2,3,4,5,6-Pentafluoroheptanes",

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-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.",

keywords = "MEDICINAL CHEMISTRY, FLUORINE",

author = "Daniel Farran and Slawin, {Alexandra M. Z.} and Peer Kirsch and David O'Hagan",

year = "2009",

month = sep,

day = "18",

doi = "10.1021/jo901360e",

language = "English",

volume = "74",

pages = "7168--7171",

journal = "The Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society (ACS)",

number = "18",

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TY - JOUR

T1 - Diastereoselective Synthesis of 2,3,4,5,6-Pentafluoroheptanes

AU - Farran, Daniel

AU - Slawin, Alexandra M. Z.

AU - Kirsch, Peer

AU - O'Hagan, David

PY - 2009/9/18

Y1 - 2009/9/18

N2 - 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.

AB - 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.

KW - MEDICINAL CHEMISTRY

KW - FLUORINE

U2 - 10.1021/jo901360e

DO - 10.1021/jo901360e

M3 - Article

SN - 0022-3263

VL - 74

SP - 7168

EP - 7171

JO - The Journal of Organic Chemistry

JF - The Journal of Organic Chemistry

IS - 18

ER -

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

Abstract

Keywords

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Synthesis and properties of novel sequen: Synthesis and properties of novel sequentially fluorinated motifs in organcic chemistry

Cite this