Fluorination of some highly functionalized cycloalkanes: chemoselectivity and substrate dependence

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

doi:10.3762/bjoc.13.233

Fluorination of some highly functionalized cycloalkanes: chemoselectivity and substrate dependence

Beilstein J Org Chem. 2017 Nov 6:13:2364-2371. doi: 10.3762/bjoc.13.233. eCollection 2017.

Authors

Attila Márió Remete¹, Melinda Nonn², Santos Fustero³, Matti Haukka⁴, Ferenc Fülöp^{1

2}, Loránd Kiss¹

Affiliations

¹ Institute of Pharmaceutical Chemistry, University of Szeged, H-6720 Szeged, Eötvös u. 6, Hungary.
² MTA-SZTE Stereochemistry Research Group, Hungarian Academy of Sciences, H-6720 Szeged, Eötvös u. 6, Hungary.
³ Departamento de Química Orgánica, Facultad de Farmàcia, Universidad de Valencia, Av. Vicente Andrés Estellés, s/n 46100 Valencia, Spain.
⁴ Department of Chemistry, University of Jyväskylä, FIN-40014, Jyväskylä, Finland.

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.

Keywords: amino acids; chemoselectivity; fluorine; functionalization; stereoisomers.