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Issue 25, 2020
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From reactive carbenes to chiral polyether macrocycles in two steps – synthesis and applications made easy?

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Abstract

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.

Graphical abstract: From reactive carbenes to chiral polyether macrocycles in two steps – synthesis and applications made easy?

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Article information


Submitted
20 Feb 2020
Accepted
11 Mar 2020
First published
12 Mar 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020,11, 6362-6369
Article type
Minireview

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

A. Homberg and J. Lacour, Chem. Sci., 2020, 11, 6362
DOI: 10.1039/D0SC01011A

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