The Asymmetry is Derived from Mechanical Interlocking of Achiral Axle and Achiral Ring Components –Syntheses and Properties of Optically Pure [2]Rotaxanes

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...

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Bibliographic Details
Published inSymmetry (Basel) Vol. 10; no. 1; p. 20
Main Authors Hirose, Keiji, Ukimi, Masaya, Ueda, Shota, Onoda, Chie, Kano, Ryohei, Tsuda, Kyosuke, Hinohara, Yuko, Tobe, Yoshito
Format Journal Article
LanguageEnglish
Published Basel MDPI AG 01.01.2018
Subjects
aminolysis
Chirality
mecanostereochemistery
mechanical chirality
rotaxane
Rotaxanes
supramolecular chirality
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Summary: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.
ISSN:2073-8994
2073-8994
DOI:10.3390/sym10010020