Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 27, Issue 36, Pages 9313-9319Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202005479
Keywords
asymmetric catalysis; azahelicene-like molecules; cyanodiynes; [2+2+2] cycloaddition; circularly polarized luminescence
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Funding
- JSPS (Japan) [19H00893, 17H06173]
- CREST from JST (Japan) [JPMJCR19R2]
- Grants-in-Aid for Scientific Research [17H06173, 19H00893] Funding Source: KAKEN
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Enantioselective synthesis of aza[6] and [7]helicene-like molecules was achieved through a specific catalytic system, yielding a highly enantioselective S-shaped double aza[6]helicene-like molecule with good fluorescent quantum yields and chiroptical responses under various conditions.
The enantioselective synthesis of aza[6] and [7]helicene-like molecules have been achieved by the cationic rhodium(I)/axially chiral biaryl bisphosphine complex-catalyzed intramolecular [2+2+2] cycloaddition of cyanodiynes. This protocol was successfully applied to the diastereo- and enantioselective synthesis of an S-shaped double aza[6]helicene-like molecule with a high ee value of 89 %. Although no epimerization and racemization were observed in the double carbo[6]helicene-like molecule at 80 degrees C, epimerization and racemization of the double aza[6]helicene-like molecule proceeded at 80 degrees C. This double aza[6]helicene-like molecule showed good fluorescent quantum yields and chiroptical responses under both neutral and acidic conditions.
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