From reactive carbenes to chiral polyether macrocycles in two steps - synthesis and applications made easy?


Journal

Chemical science
ISSN: 2041-6520
Titre abrégé: Chem Sci
Pays: England
ID NLM: 101545951

Informations de publication

Date de publication:
12 Mar 2020
Historique:
entrez: 7 6 2021
pubmed: 12 3 2020
medline: 12 3 2020
Statut: epublish

Résumé

Chiral polyether macrocycles are versatile molecules. For their preparation, original two-step procedures were recently developed and present the advantages of high concentration conditions and simple starting reagents (stable diazo reagents, small cyclic ethers, aliphatic or aromatic amines). Enantiopure materials are readily afforded by CSP-HPLC on a semi-preparative scale. Flexibility and adaptability in the macrocyclic design are provided by a large selection of amines to choose from while the ring size and chemical nature are controlled by the choice of 5 to 7-membered cyclic ether precursors. Such macrocycles have already been used as asymmetric catalysts, mono and ditopic receptors, fluorescent sensors and probes, and chiroptical reversible switches.

Identifiants

pubmed: 34094103
doi: 10.1039/d0sc01011a
pii: d0sc01011a
pmc: PMC8152409
doi:

Types de publication

Journal Article Review

Langues

eng

Pagination

6362-6369

Informations de copyright

This journal is © The Royal Society of Chemistry.

Déclaration de conflit d'intérêts

There are no conflicts to declare.

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Auteurs

Alexandre Homberg (A)

Department of Organic Chemistry, University of Geneva Quai Ernest Ansermet 30 1211 Geneva 4 Switzerland Jerome.lacour@unige.ch.

Jérôme Lacour (J)

Department of Organic Chemistry, University of Geneva Quai Ernest Ansermet 30 1211 Geneva 4 Switzerland Jerome.lacour@unige.ch.

Classifications MeSH