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Symmetry 2018, 10(1), 20; https://doi.org/10.3390/sym10010020

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

1
Graduate School of Engineering Science, Osaka University, 1-3 Machikaneyama, Toyonaka, Osaka 560-8531, Japan
2
The Institute of Scientific and Industrial Research, Osaka University, 8-1 Mihogaoka, Ibaraki, Osaka 567-0047, Japan
*
Author to whom correspondence should be addressed.
Received: 25 November 2017 / Revised: 20 December 2017 / Accepted: 27 December 2017 / Published: 9 January 2018
(This article belongs to the Special Issue Chiral Auxiliaries and Chirogenesis)
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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. View Full-Text
Keywords: mechanical chirality; mecanostereochemistery; supramolecular chirality; rotaxane; aminolysis mechanical chirality; mecanostereochemistery; supramolecular chirality; rotaxane; aminolysis
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Hirose, K.; Ukimi, M.; Ueda, S.; Onoda, C.; Kano, R.; Tsuda, K.; Hinohara, Y.; Tobe, Y. The Asymmetry is Derived from Mechanical Interlocking of Achiral Axle and Achiral Ring Components –Syntheses and Properties of Optically Pure [2]Rotaxanes–. Symmetry 2018, 10, 20.

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