Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 26, Issue 55, Pages 12579-12588Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202001450
Keywords
cycloadditions; enantioselective catalysis; planar chiral bent cyclophanes; polycyclic aromatic hydrocarbons; rhodium
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Funding
- JSPS (Japan) [JP19H00893, JP18H04504, 20H04661, 17J08763]
- Umicore
- Grants-in-Aid for Scientific Research [20H04661, 17J08763] Funding Source: KAKEN
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The enantioselective synthesis of polycyclic aromatic hydrocarbon (PAH)-based planar chiral cyclophanes was achieved for the first time by the rhodium-catalyzed intramolecular regio- and enantioselective [2+2+2] cycloaddition of tethered diyne-benzofulvenes followed by stepwise oxidative transformations. The thus synthesized planar chiral bent cyclophanes, that possess bent p-terphenyl- and 9-fluorenone-cores, were converted to 9-fluorenol-based ones with excellent ee values of > 99% by diastereoselective 1,2-reduction. These 9-fluorenol-based cyclophanes exhibited high fluorescence quantum yields, which were significantly higher than that of an acyclic reference molecule (78-82% vs. 48%). The bending effect on the chiroptical property was also examined, which revealed that the anisotropy factors (gabs values) for electronic circular dichroism (ECD) of these 9-fluorenol-based planar chiral bent cyclophanes increase as the tether length becomes shorter.
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