The asymmetry is derived from mechanical interlocking of achiral axle and achiral ring components -syntheses and properties of optically pure [2]rotaxanes-

Keiji Hirose*, Masaya Ukimi, Shota Ueda, Chie Onoda, Ryohei Kano, Kyosuke Tsuda, Yuko Hinohara, Tobe Yoshito

*Corresponding author for this work

Research output: Contribution to journalArticle

11 Scopus citations

Abstract

Rotaxanes consisting of achiral axle and achiral ring components can possess supramolecular chirality due to their unique geometrical architectures. To synthesize such chiral rotaxanes, we adapted a prerotaxane method based on aminolysis of a metacyclophane type prerotaxane that had planar chirality, which is composed of an achiral stopper unit and a crown ether type ring component. The prerotaxanes were well resolved using chiral HPLC into a pair of enantiomerically pure prerotaxanes, which were transferred into corresponding chiral rotaxanes, respectively. Obtained chiral rotaxanes were revealed to have considerable enantioselectivity.

Original languageEnglish
Article number20
JournalSymmetry
Volume10
Issue number1
DOIs
StatePublished - 1 Jan 2018

Keywords

  • Aminolysis
  • Mecanostereochemistery
  • Mechanical chirality
  • Rotaxane
  • Supramolecular chirality

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