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Article Dans Une Revue Chemical Science Année : 2021

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

Résumé

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.

Domaines

Chimie
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Origine : Publication financée par une institution

Dates et versions

hal-03105942 , version 1 (11-01-2021)

Identifiants

Citer

Noël Pairault, Adrien Bessaguet, Romain Barat, Lucas Frédéric, Grégory Pieters, et al.. Diastereoselective synthesis of [1]rotaxanes via an active metal template strategy. Chemical Science, 2021, 12 (7), pp.2521-2526. ⟨10.1039/d0sc05369d⟩. ⟨hal-03105942⟩
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