Heterobifunctional rotaxanes featuring two chiral subunits – synthesis and application in asymmetric organocatalysis

Kauerhof, Dana; Riebe, Jan; Vonnemann, Christoph J.; Thiele, Maike; Jansen, Dennis; Niemeyer, Jochen

doi:10.1039/d3cc05482a

Chem. Commun.

2024

DOI: 10.1039/d3cc05482a

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Heterobifunctional rotaxanes featuring two chiral subunits – synthesis and application in asymmetric organocatalysis

Dana Kauerhof,

Jan Riebe,

Christoph J. Vonnemann

et al.

Abstract: Rotaxanes can serve as scaffolds for the generation of bifunctional catalysts. We have now generated acid-base functionalized rotaxanes featuring two chiral subunits. The mechanical bond leads to increased reaction rates...

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Cited by 3 publications

References 38 publications

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Multimodal Molecular Motion in the Rotaxanes and Catenanes Incorporating Flexible Calix[n]phyrin Stations

Grzelczak,

Basak,

Trzaskowski

et al. 2024

Angewandte Chemie

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The synthesis of [2]rotaxanes stoppered with one or two dipyrromethane groups opened a route for the construction of mechanically interlocked molecules incorporating various porphyrinoid stations. The exploitation of those precursors allowed for the creation of [3]rotaxanes and [2]catenanes based on the calix[4]phyrin motif, presenting intriguing molecular dynamics. The intrinsic flexibility of the porphyrinoid allowed the introduction of a new type of molecular motion within the rotaxanes, termed fluttering. The latter involved a bending of the axle, interconverting two angular‐shaped stereoisomers of the rotaxane through a planarised transition state. Simple chemical transformations, i.e. methylation and (de)protonation of [3]rotaxane and [2]catenane allowed for the controllable transformations within the conformationally flexible calix[4]phyrin‐incorporated mechanically interlocked porphyrinoids.

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Multimodal Molecular Motion in the Rotaxanes and Catenanes Incorporating Flexible Calix[n]phyrin Stations

Grzelczak,

Basak,

Trzaskowski

et al. 2024

Angewandte Chemie

View full text Add to dashboard Cite

show abstract

Multimodal Molecular Motion in the Rotaxanes and Catenanes Incorporating Flexible Calix[n]phyrin Stations

Grzelczak,

Basak,

Trzaskowski

et al. 2024

Angew Chem Int Ed

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Steric Engineering of Rotaxane Catalysts: Benefits and Limits of Using the Mechanical Bond in Catalyst Design

Struth,

Jansen,

Pairault

et al. 2024

Chemistry A European J

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The mechanical bond is emerging as a novel design element in catalyst development. Here, we report a series of 1,1´‑binaphthyl‐2,2´‐diol (BINOL) based catalysts in which the number of interlocked macrocycles is varied. Unsurprisingly, the macrocycles have a profound steric influence on the catalytic performance of these molecules. However, in the enantioselective transformations examined, the macrocycles are detrimental to catalyst stereoselectivity whereas in lactide polymerization, they increase the molecular weight of the polymeric product.

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Heterobifunctional rotaxanes featuring two chiral subunits – synthesis and application in asymmetric organocatalysis

Abstract: Rotaxanes can serve as scaffolds for the generation of bifunctional catalysts. We have now generated acid-base functionalized rotaxanes featuring two chiral subunits. The mechanical bond leads to increased reaction rates...

Cited by 3 publications

References 38 publications

Multimodal Molecular Motion in the Rotaxanes and Catenanes Incorporating Flexible Calix[n]phyrin Stations

Multimodal Molecular Motion in the Rotaxanes and Catenanes Incorporating Flexible Calix[n]phyrin Stations

Multimodal Molecular Motion in the Rotaxanes and Catenanes Incorporating Flexible Calix[n]phyrin Stations

Steric Engineering of Rotaxane Catalysts: Benefits and Limits of Using the Mechanical Bond in Catalyst Design

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