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

ABSTRACT: 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.

SUBMITTER: Pairault N

PROVIDER: S-EPMC8179266 | biostudies-literature | 2020 Dec

REPOSITORIES: biostudies-literature

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Diastereoselective synthesis of [1]rotaxanes <i>via</i> an active metal template strategy.

Pairault Noël N Bessaguet Adrien A Barat Romain R Frédéric Lucas L Pieters Grégory G Crassous Jeanne J Opalinski Isabelle I Papot Sébastien S

Chemical science 20201229 7

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 labi ...[more]

PMID: 34164020

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