Fluorination of some highly functionalized cycloalkanes: chemoselectivity and substrate dependence.

Attila Márió Remete,Loránd Kiss,Ferenc Fülöp,Santos Fustero,Melinda Nonn,Matti Haukka

doi:10.3762/bjoc.13.233

Abstract

A study exploring the chemical behavior of some dihydroxylated β-amino ester stereo- and regioisomers, derived from unsaturated cyclic β-amino acids is described. The nucleophilic fluorinations involving hydroxy–fluorine exchange of some highly functionalized alicyclic diol derivatives have been carried out in view of selective fluorination, investigating substrate dependence, neighboring group assistance and chemodifferentiation.

Highlights

Fluorinated molecules exert an ever-increasing impact in medicinal chemistry thanks to their valuable biological properties
Numerous drugs introduced to the market nowadays contain fluorine, and their number is expected to continuously increase in years to come [1,2]
The most common approach is the exchange of a hydroxy group for fluorine, taking place, in general, by inver

Summary

Introduction

Fluorinated molecules exert an ever-increasing impact in medicinal chemistry thanks to their valuable biological properties. There is a high demand in synthetic organic and medicinal chemistry for both, the synthesis of novel fluorinated biomolecules and the development of selective and controlled efficient fluorination procedures. This high interest is clearly demonstrated by the number of various published papers on the field, and related recent comprehensive reviews [3,4,5,6,7,8,9,10,11,12]. The nucleophilic fluorination with commercially available organic fluorinating agents (e.g., DAST, Deoxofluor, Fluolead, XtalFluor-E or XtalFluor-M) is a widely used approach for the introduction of a fluorine atom into an organic molecule. The most common approach is the exchange of a hydroxy group for fluorine, taking place, in general, by inver-

Methods

Results

Conclusion