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The synthesis of the 2,3-difluorobutan-1,4-diol diastereomers

The synthesis of the 2,3-difluorobutan-1,4-diol diastereomers
The synthesis of the 2,3-difluorobutan-1,4-diol diastereomers
The diastereoselective synthesis of fluorinated building blocks that contain chiral fluorine substituents is of interest. Here we describe optimisation efforts in the synthesis of anti-2,3-difluorobutane-1,4-diol, as well as the synthesis of the corresponding syn-diastereomer. Both targets were synthesised using an epoxide opening strategy.
acetal isomerization, deoxyfluorination, epoxide opening, fluorinated building block, vicinal difluoride
1860-5397
2883-2887
Szpera, Robert
fc00a238-112f-4646-9783-6f9309456c09
Kovalenko, Nadia
1b986e0a-3eaa-49bc-a5e0-163e8c9e1cf9
Natarajan, Kalaiselvi
d653b063-ca32-4474-bf14-521fa54602d0
Paillard, Nina
f83e0bb1-f00c-4278-bd76-f0e494c2e0ae
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba
Szpera, Robert
fc00a238-112f-4646-9783-6f9309456c09
Kovalenko, Nadia
1b986e0a-3eaa-49bc-a5e0-163e8c9e1cf9
Natarajan, Kalaiselvi
d653b063-ca32-4474-bf14-521fa54602d0
Paillard, Nina
f83e0bb1-f00c-4278-bd76-f0e494c2e0ae
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba

Szpera, Robert, Kovalenko, Nadia, Natarajan, Kalaiselvi, Paillard, Nina and Linclau, Bruno (2017) The synthesis of the 2,3-difluorobutan-1,4-diol diastereomers. Beilstein Journal of Organic Chemistry, 13, 2883-2887. (doi:10.3762/bjoc.13.280).

Record type: Article

Abstract

The diastereoselective synthesis of fluorinated building blocks that contain chiral fluorine substituents is of interest. Here we describe optimisation efforts in the synthesis of anti-2,3-difluorobutane-1,4-diol, as well as the synthesis of the corresponding syn-diastereomer. Both targets were synthesised using an epoxide opening strategy.

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Accepted/In Press date: 13 December 2017
e-pub ahead of print date: 27 December 2017
Keywords: acetal isomerization, deoxyfluorination, epoxide opening, fluorinated building block, vicinal difluoride

Identifiers

Local EPrints ID: 416831
URI: http://eprints.soton.ac.uk/id/eprint/416831
ISSN: 1860-5397
PURE UUID: 684e85f5-899b-4286-873d-dcd20bc02c29
ORCID for Bruno Linclau: ORCID iD orcid.org/0000-0001-8762-0170

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Date deposited: 11 Jan 2018 17:30
Last modified: 22 Nov 2021 02:45

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Contributors

Author: Robert Szpera
Author: Nadia Kovalenko
Author: Kalaiselvi Natarajan
Author: Nina Paillard
Author: Bruno Linclau ORCID iD

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