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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
a   Institute of Pharmaceutical Chemistry, University of Szeged, 6720 Szeged, Eötvös u. 6, Hungary
b   Interdisciplinary Excellence Centre, Institute of Pharmaceutical Chemistry, University of Szeged, 6720 Szeged, Eötvös u. 6, Hungary
c   MTA-SZTE Stereochemistry Research Group, Hungarian Academy of Sciences, 6720 Szeged, Eötvös u. 6, Hungary
,
Dominika Kara
a   Institute of Pharmaceutical Chemistry, University of Szeged, 6720 Szeged, Eötvös u. 6, Hungary
b   Interdisciplinary Excellence Centre, Institute of Pharmaceutical Chemistry, University of Szeged, 6720 Szeged, Eötvös u. 6, Hungary
,
Lamiaa Ouchakour
a   Institute of Pharmaceutical Chemistry, University of Szeged, 6720 Szeged, Eötvös u. 6, Hungary
b   Interdisciplinary Excellence Centre, Institute of Pharmaceutical Chemistry, University of Szeged, 6720 Szeged, Eötvös u. 6, Hungary
,
Enikő Forró
a   Institute of Pharmaceutical Chemistry, University of Szeged, 6720 Szeged, Eötvös u. 6, Hungary
,
Matti Haukka
d   Department of Chemistry, University of Jyväskylä, 40014, Jyväskylä, Finland
,
Loránd Kiss∗
a   Institute of Pharmaceutical Chemistry, University of Szeged, 6720 Szeged, Eötvös u. 6, Hungary
b   Interdisciplinary Excellence Centre, Institute of Pharmaceutical Chemistry, University of Szeged, 6720 Szeged, Eötvös u. 6, Hungary
› Author AffiliationsWe are grateful to the Hungarian Research Foundation (NKFIH Nos K 119282 and K 129049) for financial support. The financial support of the GINOP-2.3.2-15-2016-00014 project is also acknowledged. This research was supported by the EU-funded Hungarian grant EFOP-3.6.1-16-2016-00008. Ministry of Human Capacities, Hungary (grant 20391-3/2018/FEKUSTRAT) is also acknowledged.
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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

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1706637.
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Publication History

Received: 29 October 2020

Accepted after revision: 13 November 2020

Article published online:
14 December 2020

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