Issue 23, 2013
From the journal:

Organic & Biomolecular Chemistry

Conformational regulation of substituted azepanes through selective monofluorination†

Alpesh Ramanlal Patel,a   Graham Ball,b   Luke Hunterb  and  Fei Liu*a  

* Corresponding authors

a Department of Chemistry and Biomolecular Sciences, Macquarie University, Sydney NSW 2109, Australia
E-mail: fei.liu@mq.edu.au

b School of Chemistry, The University of New South Wales, Sydney NSW 2052, Australia

Abstract

Substituted azepanes are common bioactive epitopes with flexible ring structures. The conformational effects of monofluorination in model azepane rings were investigated by 1H NMR spectroscopy and computational modelling. A single fluorine atom, installed diastereoselectively, was found to bias the azepane ring to one major conformation for one diastereomer.

Graphical abstract: Conformational regulation of substituted azepanes through selective monofluorination

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Article information

DOI
https://doi.org/10.1039/C3OB40391B
Article type
Communication
Submitted
22 Feb 2013
Accepted
23 Apr 2013
First published
24 Apr 2013

Org. Biomol. Chem., 2013,11, 3781-3785

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Conformational regulation of substituted azepanes through selective monofluorination

A. R. Patel, G. Ball, L. Hunter and F. Liu, Org. Biomol. Chem., 2013, 11, 3781 DOI: 10.1039/C3OB40391B

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