Diversity-oriented Functionalization of Cyclodienes Through Selective Cycloaddition/Ring-opening/Cross-metathesis Protocols; Transformation of a "Flatland" into Three-dimensional Scaffolds With Stereo- and Regiocontrol.

cross-metathesis functionalization selective coupling β-lactam, isoxazoline

Journal

Chemical record (New York, N.Y.)
ISSN: 1528-0691
Titre abrégé: Chem Rec
Pays: United States
ID NLM: 101085550

Informations de publication

Date de publication:
Oct 2020
Historique:
received: 11 06 2020
revised: 05 07 2020
accepted: 06 07 2020
pubmed: 29 7 2020
medline: 29 7 2020
entrez: 29 7 2020
Statut: ppublish

Résumé

This article presents selective transformations of some readily available cyclodienes through simple chemical procedures into novel functionalized small-molecular entities. The syntheses hereby described involved selective cycloadditions, followed by ring-opening metathesis of the resulting β-lactam or isoxazoline derivatives and selective cross-metathesis by differentiation of the olefin bonds on the alkenylated heterocycles. The cross-metathesis transformations have been detailed, which were performed under various experimental conditions with the aim of exploring chemodiscrimination of the olefin bonds and delivering the corresponding functionalized β-lactam or isoxazoline derivatives.

Identifiants

pubmed: 32720742
doi: 10.1002/tcr.202000070
doi:

Types de publication

Journal Article Review

Langues

eng

Sous-ensembles de citation

IM

Pagination

1129-1141

Subventions

Organisme : Hungarian Research Foundation
ID : K 119282
Organisme : GINOP
ID : 2.3.2-15-2016-00060
Organisme : EU-funded Hungarian grant
ID : EFOP-3.6.1-16-2016-00008
Organisme : Ministry of Human Capacities, Hungary
ID : 20391-3/2018/FEKUSTRAT

Informations de copyright

© 2020 The Chemical Society of Japan & Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Auteurs

Loránd Kiss (L)

Institute of Pharmaceutical Chemistry, University of Szeged, H-6720, Szeged, Eötvös u. 6, Hungary.
University of Szeged, I, nterdisciplinary Excellence Centre, Institute of Pharmaceutical Chemistry, H-6720, Szeged, Eötvös u. 6, Hungary.

Zsanett Benke (Z)

Institute of Pharmaceutical Chemistry, University of Szeged, H-6720, Szeged, Eötvös u. 6, Hungary.
University of Szeged, I, nterdisciplinary Excellence Centre, Institute of Pharmaceutical Chemistry, H-6720, Szeged, Eötvös u. 6, Hungary.

Attila M Remete (AM)

Institute of Pharmaceutical Chemistry, University of Szeged, H-6720, Szeged, Eötvös u. 6, Hungary.
University of Szeged, I, nterdisciplinary Excellence Centre, Institute of Pharmaceutical Chemistry, H-6720, Szeged, Eötvös u. 6, Hungary.

Ferenc Fülöp (F)

Institute of Pharmaceutical Chemistry, University of Szeged, H-6720, Szeged, Eötvös u. 6, Hungary.
University of Szeged, I, nterdisciplinary Excellence Centre, Institute of Pharmaceutical Chemistry, H-6720, Szeged, Eötvös u. 6, Hungary.
MTA-SZTE Stereochemistry Research Group, Hungarian Academy of Sciences, H-6720, Szeged, Eötvös u. 6, Hungary.

Classifications MeSH