Journal
CHEMICAL SCIENCE
Volume 12, Issue 7, Pages 2521-2526Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0sc05369d
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- Ministere de l'enseignement superieur, de la recherche et de l'innovation
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This study presents the first diastereoselective synthesis of mechanically planar chiral [1]rotaxanes using the active template Cu-mediated alkyne-azide cycloaddition reaction. This synthetic method allows for the preparation of a variety of mechanically planar chiral [1]rotaxanes, paving the way for the study of their properties and potential applications.
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.
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