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From reactive carbenes to chiral polyether macrocycles in two steps – synthesis and applications made easy?
Chemical Science ( IF 7.6 ) Pub Date : 2020-03-12 , DOI: 10.1039/d0sc01011a
Alexandre Homberg 1 , Jérôme Lacour 1
Affiliation  

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.

中文翻译:

从反应性卡宾到手性聚醚大环化合物只需两步——合成和应用变得简单?

手性聚醚大环化合物是多用途分子。对于它们的制备,最近开发了原始的两步程序,并具有高浓度条件和简单起始试剂(稳定的重氮试剂、小环醚、脂肪族或芳香胺)的优点。通过半制备规模的 CSP-HPLC 可以轻松获得对映体纯材料。大环设计的灵活性和适应性是由大量可供选择的胺提供的,而环的大小和化学性质是通过选择 5 至 7 元环醚前体来控制的。此类大环化合物已被用作不对称催化剂、单位和双位受体、荧光传感器和探针以及手性光学可逆开关。
更新日期:2020-03-12
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