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July 7, 2026Angewandte Chemie

A General and Scalable Chiral Surrogate Rotaxane Strategy for Highly Enantioenriched Mechanically Planar Chiral Rotaxanes

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Authors

SLS Chin LeeYLYi‐Hung LiuSCSheng‐Hsien Chiu

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Overview

Randomized trial demonstrates a new method for synthesizing highly enantioenriched mechanically planar chiral rotaxanes, indicating potential for broader applications.

Key Points

  • The aim is to develop a scalable strategy for synthesizing mechanically planar chiral rotaxanes with high optical purity.
  • Utilized a chiral surrogate rotaxane strategy for synthesis.
  • Generated a diastereomeric CSR via an S N 2 interlocking process.
  • Displaced a chiral nucleophilic auxiliary with a semidumbbell-shaped nucleophile.
  • Achieved mechanically planar chiral rotaxanes with optical purity of ca. 99.6% ee.
  • Synthesized all three stereoisomers of a [3]rotaxane with 99.8% stereoisomeric purity.
  • Quantitative recovery of the auxiliary was accomplished, enhancing efficiency.

Cite This Study

Lee et al. (2026) studied this question.

synapsesocial.com/papers/6a4c9754331bc25c9e5f43e2https://doi.org/10.1002/ange.8987942
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Also Consider

Synapse has enriched 5 closely related papers on similar clinical questions. Consider them for comparative context:

  1. 1The Asymmetry is Derived from Mechanical Interlocking of Achiral Axle and Achiral Ring Components –Syntheses and Properties of Optically Pure [2]Rotaxanes–2018 · 54 citations
  2. 2Synthesis of a Mechanically Planar Chiral Rotaxane Ligand for Enantioselective Catalysis2020 · 177 citations
  3. 3Dynamic Control of Chiral Space Through Local Symmetry Breaking in a Rotaxane Organocatalyst2019 · 28 citations
  4. 4Synthesis of Mechanically Planar Chiral <i>rac-</i>[2]Rotaxanes by Partitioning of an Achiral [2]Rotaxane: Stereoinversion Induced by Shuttling2017 · 45 citations
  5. 5Enantioselective Synthesis of Mechanically Planar Chiral Rotaxanes by an Asymmetric Povarov Reaction‐Enabled Desymmetrization2025 · 7 citations