Cooperative Conformational Regulation in N-Heterocyclic Fluorohydrins

Alpesh Ramanlal Patel, Fei Liu*

*Corresponding author for this work

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

Seven-membered N-heterocycles are flexible ring structures, and their conformational control is important to their bioactivity. Our prior work shows that stereoselective monofluorination, if installed diastereoselectively, can bias a seven-membered, substituted azepane ring to one major conformation. However, multiple fluorination may not provide as much conformational bias due to conflicting effects. Here we show in our model azepane system that fluorohydrins can confer strong conformational bias if the relative configuration of the fluorine and hydroxy substitutent is appropriate to enable cooperative conformational control.

Original languageEnglish
Pages (from-to)50-56
Number of pages7
JournalAustralian Journal of Chemistry
Volume68
Issue number1
DOIs
Publication statusPublished - 2015

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