2423-73-6Relevant articles and documents
Diastereoselective synthesis of [1]rotaxanesviaan active metal template strategy
Pairault, No?l,Bessaguet, Adrien,Barat, Romain,Frédéric, Lucas,Pieters, Grégory,Crassous, Jeanne,Opalinski, Isabelle,Papot, Sébastien
, p. 2521 - 2526 (2021/03/01)
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.