Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 83, Issue 10, Pages 5523-5538Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b00538
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Funding
- Czech Science Foundation [16-08294S]
- Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences [RVO: 61388963]
- German Academic Exchange Service (DAAD-fellowship) [57314603]
- Ministry of Education, Youth and Sports of the Czech Republic [LM2015073]
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Alternative ways of preparing nonracemic 2-amino[6]helicene derivatives were explored. The enantioselective [2 + 2 + 2] cycloisomerization of a nonchiral triyne under Ni(cod)(2)/(R)-QUINAP catalysis delivered the enantioenriched (+)-(P)-2-aminodibenzo[6]helicene derivative in 67% ee. An ultimate point-to-helical chirality transfer was observed in the cyclization of enantiopure triynes mediated by Ni(CO)(2)(PPh3)(2) affording (-)-(M)- or (+)-(P)-7,8-bis(p-tolyl)hexahelicen-2-amine in >99% ee as well as its benzoderivative in >99% ee. The latter mode of stereocontrol was inefficient for a 2-aminobenzo[6]helicene congener with an embedded five-membered ring. The rac-, (-)-(M)-, and (+)-(P)-7,8-bis(p-tolyl)hexahelicen-2-amines formed Langmuir monolayers at the air water interface featuring practically identical surface pressure vs mean molecular area isotherms. The corresponding Langmuir-Blodgett films on quartz or silicon substrates were characterized by UV vis/ECD spectroscopy and AFM microscopy, respectively.
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