Issue 19, 2011
From the journal:

Organic & Biomolecular Chemistry

Regio- and diastereoselective fluorination of alicyclic β-amino acids†

Loránd Kiss,a   Enikő Forró,a   Santos Fusteroc  and  Ferenc Fülöp*ab  

* Corresponding authors

a Institute of Pharmaceutical Chemistry, University of Szeged, Szeged, Eötvös u. 6, Szeged, Hungary

b Research Group of Stereochemistry of the Hungarian Academy of Sciences, University of Szeged, Szeged, Eötvös u. 6, Szeged, Hungary

c Departamento de Química Orgánica, Facultad de Farmacia, Universidad de Valencia, Burjassot, Valencia, Spain

Abstract

A regio- and stereoselective approach to fluorinated β-aminocyclohexene or cyclohexane esters has been developed, starting from a bicyclic β-lactam (1). The procedure involves six or seven steps, based on regio- and stereoselective iodolactonization, lactone opening and hydroxy–fluorine exchange. The method has been extended to the synthesis of fluorinated amino ester enantiomers.

Graphical abstract: Regio- and diastereoselective fluorination of alicyclic β-amino acids

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Article information

DOI
https://doi.org/10.1039/C1OB05648D
Article type
Paper
Submitted
26 Apr 2011
Accepted
16 Jun 2011
First published
16 Jun 2011

Org. Biomol. Chem., 2011,9, 6528-6534

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Regio- and diastereoselective fluorination of alicyclic β-amino acids

L. Kiss, E. Forró, S. Fustero and F. Fülöp, Org. Biomol. Chem., 2011, 9, 6528 DOI: 10.1039/C1OB05648D

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