期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2018, 期 37, 页码 5164-5178出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201800541
关键词
Asymmetric synthesis; Chirality; Cyclotrimerization; Fused-ring systems; Nitrogen heterocycles
资金
- Czech Science Foundation [16-08294S]
- Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences [RVO: 61388963]
A versatile asymmetric synthesis of five C-2 symmetric enantio- and diastereopure bioxa[5]- and bioxa[6]helicene 2,2-bipyridines was developed. It relied either on a double intramolecular [2+2+2] cycloisomerization of dicyanotetrayne (forming simultaneously the 2,2-bipyridine unit and biazaoxahelicene backbone) or one-pot/sequential intramolecular [2+2+2] cycloisomerization of triyne accompanied by an intermolecular haloazaoxahelicene reductive homocoupling. We reached an effective central-to-helical-to-axial chirality transfer that was controlled by the 1,3-allylic-type strain and sterically constricted atropoisomerization of the embedded 2,2-bipyridine unit. The chiroptical properties of the bioxahelicene 2,2-bipyridines were studied along with their fluorescence properties.
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