- From reactive carbenes to chiral polyether macrocycles in two steps – synthesis and applications made easy?
Alexandre Homberg, Jérôme Lacour
Chem. Sci., in press
Chiral polyether macrocycles are versatile molecules. For their preparation, original two-step procedures were recently developed and present the advantage 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 semi preparative scale. Flexibility and adaptability in the macrocyclic design is provided by a large selection of amines to choose from while ring size and chemical nature is controlled by the choice of 5 to 7-membered cyclic ether precursors. Such macrocycles have been used already as asymmetric catalysts, mono and ditopic receptors, fluorescent sensors and probes, and chiroptical reversible switches.