Issue 40, 2018

Minimising conformational bias in fluoroprolines through vicinal difluorination

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 instil opposite conformational effects, as a suitable probe for fluorine NMR studies.

Graphical abstract: Minimising conformational bias in fluoroprolines through vicinal difluorination

Supplementary files

Article information

Article type
Communication
Submitted
22 2 2018
Accepted
27 3 2018
First published
16 4 2018
This article is Open Access
Creative Commons BY license

Chem. Commun., 2018,54, 5118-5121

Minimising conformational bias in fluoroprolines through vicinal difluorination

G. Hofman, E. Ottoy, M. E. Light, B. Kieffer, I. Kuprov, J. C. Martins, D. Sinnaeve and B. Linclau, Chem. Commun., 2018, 54, 5118 DOI: 10.1039/C8CC01493K

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