Minimising conformational bias in fluoroprolines through vicinal difluorination‡

Literature Information

Publication Date 2018-04-16
DOI 10.1039/C8CC01493K
Impact Factor 6.222
Authors

Emile Ottoy, Mark E. Light, Bruno Kieffer, Ilya Kuprov, Jose C. Martins, Davy Sinnaeve, Bruno Linclau


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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.

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