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Minimising conformational bias in fluoroprolines through vicinal difluorination

Minimising conformational bias in fluoroprolines through vicinal difluorination
Minimising conformational bias in fluoroprolines through vicinal difluorination
Monofluorination at the proline 4-position results in conformational effects, which is exploited for a range of applications. However, this conformational distortion is a hindrance when the natural proline conformation is important. Here we introduce (3S,4R)-3,4-difluoroproline, in which the individual fluorine atoms instill opposite conformational effects, as a suitable probe for fluorine NMR studies.
1359-7345
5118-5121
Hofman, Gert-Jan
696ede89-26ae-4a7e-88d8-0574fce74d93
Ottoy, Emile
d34b7519-7bc5-4f61-8bc8-5a0ec5584b62
Light, Mark
cf57314e-6856-491b-a8d2-2dffc452e161
Kieffer, Bruno
34187faf-4dc3-4d1b-895c-cee8ce760217
Kuprov, Ilya
bb07f28a-5038-4524-8146-e3fc8344c065
Martins, José C.
6ca83d5b-f416-4309-a2ec-fe10d5024881
Sinnaeve, Davy
1bff7c9e-d706-4318-9042-b291807752d6
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba
Hofman, Gert-Jan
696ede89-26ae-4a7e-88d8-0574fce74d93
Ottoy, Emile
d34b7519-7bc5-4f61-8bc8-5a0ec5584b62
Light, Mark
cf57314e-6856-491b-a8d2-2dffc452e161
Kieffer, Bruno
34187faf-4dc3-4d1b-895c-cee8ce760217
Kuprov, Ilya
bb07f28a-5038-4524-8146-e3fc8344c065
Martins, José C.
6ca83d5b-f416-4309-a2ec-fe10d5024881
Sinnaeve, Davy
1bff7c9e-d706-4318-9042-b291807752d6
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba

Hofman, Gert-Jan, Ottoy, Emile, Light, Mark, Kieffer, Bruno, Kuprov, Ilya, Martins, José C., Sinnaeve, Davy and Linclau, Bruno (2018) Minimising conformational bias in fluoroprolines through vicinal difluorination. Chemical Communications, 54 (40), 5118-5121. (doi:10.1039/C8CC01493K).

Record type: Article

Abstract

Monofluorination at the proline 4-position results in conformational effects, which is exploited for a range of applications. However, this conformational distortion is a hindrance when the natural proline conformation is important. Here we introduce (3S,4R)-3,4-difluoroproline, in which the individual fluorine atoms instill opposite conformational effects, as a suitable probe for fluorine NMR studies.

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Linclau_Sinnaeve_Martins manuscript - Accepted Manuscript
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Accepted/In Press date: 27 March 2018
e-pub ahead of print date: 16 April 2018
Published date: 16 April 2018

Identifiers

Local EPrints ID: 420270
URI: http://eprints.soton.ac.uk/id/eprint/420270
ISSN: 1359-7345
PURE UUID: f47f5269-2ef8-4c50-a9da-952d21dbdc1e
ORCID for Mark Light: ORCID iD orcid.org/0000-0002-0585-0843
ORCID for Ilya Kuprov: ORCID iD orcid.org/0000-0003-0430-2682
ORCID for Bruno Linclau: ORCID iD orcid.org/0000-0001-8762-0170

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Date deposited: 03 May 2018 16:30
Last modified: 15 Sep 2021 01:59

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Contributors

Author: Gert-Jan Hofman
Author: Emile Ottoy
Author: Mark Light ORCID iD
Author: Bruno Kieffer
Author: Ilya Kuprov ORCID iD
Author: José C. Martins
Author: Davy Sinnaeve
Author: Bruno Linclau ORCID iD

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