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Fluorinated cyclohexanes : synthesis of amine building blocks of the all-cis 2,3,5,6-tetrafluorocyclohexylamine motif

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Date
19/04/2017
Author
Bykova, Tetiana
Al-Maharik, Nawaf
Slawin, Alexandra M. Z.
O'Hagan, David
Keywords
All-cis tetrafluorocyclohexane motif
Deoxofluorination reactions
Fluorinated amines
Fluorinated cyclohexanes
QD Chemistry
NDAS
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Abstract
This paper reports the synthesis of three amine stereoisomers 5a–c of the tetrafluorocyclohexyl ring system, as building blocks for discovery chemistry programmes. The synthesis starts from a Birch reduction of benzonitrile, followed by an in situ methyl iodide quench. The resultant 2,5-cyclohexadiene was progressed via double epoxidations and then hydrofluorination ring opening reactions. The resultant fluorohydrin moieties were then converted to different stereoisomers of the tetrafluorocyclohexyl ring system, and then reductive hydrogenation of the nitrile delivered three amine stereoisomers. It proved necessary to place a methyl group on the cyclohexane ring in order to stabilise the compound against subsequent HF elimination. The two all-cis tetrafluorocyclohexyl isomers 5a and 5b constitute facially polarized cyclohexane rings, with fluorines on the electronegative face and hydrogens on the electropositive face.
Citation
Bykova , T , Al-Maharik , N , Slawin , A M Z & O'Hagan , D 2017 , ' Fluorinated cyclohexanes : synthesis of amine building blocks of the all-cis 2,3,5,6-tetrafluorocyclohexylamine motif ' , Beilstein Journal of Organic Chemistry , vol. 13 , pp. 728-733 . https://doi.org/10.3762/bjoc.13.72
Publication
Beilstein Journal of Organic Chemistry
Status
Peer reviewed
DOI
https://doi.org/10.3762/bjoc.13.72
ISSN
1860-5397
Type
Journal article
Rights
© 2017 Bykova et al.; licensee Beilstein-Institut. This is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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  • University of St Andrews Research
URL
http://www.beilstein-journals.org/bjoc/articles/13/72/downloads
URI
http://hdl.handle.net/10023/10797

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