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Diastereoselective synthesis of [1]rotaxanes via an active metal template strategy

2020; Royal Society of Chemistry; Volume: 12; Issue: 7 Linguagem: Inglês

10.1039/d0sc05369d

2041-6539

Noël Pairault, Adrien Bessaguet, Romain Barat, Lucas Frédéric, Grégory Pieters, Jeanne Crassous, Isabelle Tranoy‐Opalinski, Sébastien Papot,

Luminescence and Fluorescent Materials

Despite the impressive number of interlocked molecules described in the literature over the past 30 years, only a few stereoselective syntheses of mechanically chiral rotaxanes have been reported so far. In this study, we present the first diastereoselective synthesis of mechanically planar chiral [1]rotaxanes, that has been achieved using the active template Cu-mediated alkyne-azide cycloaddition reaction. This synthetic method has been applied to the preparation of a [1]rotaxane bearing a labile stopper that can then be substituted without disruption of the mechanical bond. This approach paves the way for the synthesis of a wide variety of mechanically planar chiral [1]rotaxanes, hence allowing the study of the properties and potential applications of this class of interlocked molecular architectures.