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August 1, 2026Angewandte Chemie International Edition

Stereoselective Synthesis of Mechanically Planar Chiral Rotaxanes and Mechanical Geometric Isomers From a Macrocyclic Ketone‐Based Prochiral Rotaxane

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Authors

JZJinmiao ZhouQZQinghai ZhouYMYuheng Ma

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Overview

Randomized trial develops methods to synthesize mechanical isomers in rotaxanes, suggesting improved stereocontrol.

Key Points

  • The aim is to synthesize mechanically planar chiral and geometric isomer rotaxanes using a macrocyclic ketone.
  • Design of a macrocyclic ketone-based prochiral rotaxane for synthesis.
  • Organocatalyzed asymmetric condensation with arylhydroxylamines to synthesize MPC rotaxanes.
  • Diasteselective reduction of carbonyl group in the macrocyclic ketone for MGI rotaxane formation.
  • Achieved good to high enantioselectivities for MPC rotaxanes using the designed prochiral rotaxane.
  • Developed novel MPC rotaxanes with lactam-containing macrocycles retaining enantiopurity after rearrangement.
  • Successfully formed both mechanical geometric isomers of Schill-type MGI rotaxanes through optimized reduction conditions.

Cite This Study

Zhou et al. (2026) studied this question.

synapsesocial.com/papers/6a6d98b4e258b358b3c6c67dhttps://doi.org/10.1002/anie.2661433
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  1. 1Stereoselective Synthesis of Mechanically Planar Chiral Rotaxanes and Mechanical Geometric Isomers From a Macrocyclic Ketone‐Based Prochiral Rotaxane2026
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