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Optically active distorted cyclic triptycenes: chiral stationary phases for HPLC

Author(s)
Swager, Timothy M
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Creative Commons Attribution Noncommercial 3.0 unported license https://creativecommons.org/licenses/by-nc/3.0/
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Abstract
A pair of optically active triptycene derivatives ((R,R)- and (S,S)-8) with a distorted cyclic structure were synthesized via an intramolecular etherification and evaluated as a novel chiral selector for high-performance liquid chromatography. The (R,R)- and (S,S)-8-based chiral stationary phases (CSPs) were found to be particularly effective in the resolution of axially chiral biaryl compounds. The importance of the distorted cyclic structure present in 8 for chiral recognition was demonstrated by comparisons with the corresponding non-cyclic model compound ((R,R)-9), which did not display enantioselectivity in the separation of the test racemates.
Date issued
2018-06
URI
https://hdl.handle.net/1721.1/125403
Department
Massachusetts Institute of Technology. Department of Chemistry
Journal
RSC advances
Publisher
Royal Society of Chemistry (RSC)
Citation
Ikai, Tomoyuki et al. “Optically active distorted cyclic triptycenes: chiral stationary phases for HPLC.” RSC advances 8 (2018): 20483-20487 © 2018 The Author(s)
Version: Final published version
ISSN
2046-2069

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