Diversity-Oriented Stereocontrolled Synthesis of Some Piperidine- and Azepane-Based Fluorine-Containing β-Amino Acid Derivatives

Melinda Nonn; Dominika Kara; Lamiaa Ouchakour; Enikő Forró; Matti Haukka; Loránd Kiss

doi:10.1055/s-0040-1706637

Synthesis, Table of Contents

Synthesis 2021; 53(06): 1163-1173
DOI: 10.1055/s-0040-1706637

paper

Diversity-Oriented Stereocontrolled Synthesis of Some Piperidine- and Azepane-Based Fluorine-Containing β-Amino Acid Derivatives

Melinda Nonn

^aInstitute of Pharmaceutical Chemistry, University of Szeged, 6720 Szeged, Eötvös u. 6, Hungary

^bInterdisciplinary Excellence Centre, Institute of Pharmaceutical Chemistry, University of Szeged, 6720 Szeged, Eötvös u. 6, Hungary

^cMTA-SZTE Stereochemistry Research Group, Hungarian Academy of Sciences, 6720 Szeged, Eötvös u. 6, Hungary

,

Dominika Kara

^aInstitute of Pharmaceutical Chemistry, University of Szeged, 6720 Szeged, Eötvös u. 6, Hungary

^bInterdisciplinary Excellence Centre, Institute of Pharmaceutical Chemistry, University of Szeged, 6720 Szeged, Eötvös u. 6, Hungary

,

Lamiaa Ouchakour

^aInstitute of Pharmaceutical Chemistry, University of Szeged, 6720 Szeged, Eötvös u. 6, Hungary

^bInterdisciplinary Excellence Centre, Institute of Pharmaceutical Chemistry, University of Szeged, 6720 Szeged, Eötvös u. 6, Hungary

,

Enikő Forró

^aInstitute of Pharmaceutical Chemistry, University of Szeged, 6720 Szeged, Eötvös u. 6, Hungary

,

Matti Haukka

^dDepartment of Chemistry, University of Jyväskylä, 40014, Jyväskylä, Finland

,

Loránd Kiss∗

^aInstitute of Pharmaceutical Chemistry, University of Szeged, 6720 Szeged, Eötvös u. 6, Hungary

^bInterdisciplinary Excellence Centre, Institute of Pharmaceutical Chemistry, University of Szeged, 6720 Szeged, Eötvös u. 6, Hungary

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Abstract

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Abstract

Structural diversity-oriented synthesis of some azaheterocyclic β-amino acid derivatives has been accomplished by selective functionalization of readily available cyclodienes. The stereocontrolled synthetic concept was based on the oxidative ring cleavage of unsaturated cyclic β-amino acids derived from cycloalkadiene, followed by ring closing with double reductive amination, which furnished some conformationally restricted β-amino acid derivatives with a piperidine or azepane core.

Key words

azaheterocyles - structural diversity - amino acids - stereocontrol - selectivity

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References

References

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