A General Approach to Optically Pure [5]-, [6]-, and [7]Heterohelicenes

A General Approach to Optically Pure [5]-, [6]-, and [7]Heterohelicenes

Spiral staircases: A general method for the preparation of optically pure [5]‐, [6]‐, and [7]heterohelicenes is based on a CoI‐ or Ni0‐catalyzed diastereoselective [2+2+2] cycloisomerization of centrally chiral triynes to deliver helicenes comprising two 2H‐pyran rings. The configuration, which can...

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Published in:Angewandte Chemie International Edition Vol. 51; no. 24; pp. 5857 - 5861
Main Authors: Žádný, Jaroslav, Jančařík, Andrej, Andronova, Angelina, Šámal, Michal, Vacek Chocholoušová, Jana, Vacek, Jaroslav, Pohl, Radek, Šaman, David, Císařová, Ivana, Stará, Irena G., Starý, Ivo
Format: Journal Article
Language:English
Published: Weinheim WILEY-VCH Verlag 11-06-2012
WILEY‐VCH Verlag
Wiley Subscription Services, Inc
Edition:International ed. in English
Subjects:
aromatic compounds
asymmetric synthesis
chirality
Functional groups
helical structures
heterocycles
Isomerization
Spirals
Staircases
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Summary:Spiral staircases: A general method for the preparation of optically pure [5]‐, [6]‐, and [7]heterohelicenes is based on a CoI‐ or Ni0‐catalyzed diastereoselective [2+2+2] cycloisomerization of centrally chiral triynes to deliver helicenes comprising two 2H‐pyran rings. The configuration, which can be predicted, does not depend on helicene length or functional groups present.
Bibliography:istex:A60CDE9595B5CB3D2209F5BF5DDF267CED6036BA
Ministry of Education, Youth, and Sports - No. LC512; No. MSM0021620857; No. Kontakt ME09020
Academy of Sciences of the Czech Republic - No. RVO 61388963
ArticleID:ANIE201108307
ark:/67375/WNG-9K4KC6CQ-Z
Czech Science Foundation - No. 203/09/1766; No. 203/09/1802
This work was supported by the Czech Science Foundation (203/09/1766, 203/09/1802), by the Ministry of Education, Youth, and Sports of the Czech Republic (LC512, MSM0021620857, Kontakt ME09020), and by the Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic (RVO 61388963). Dr. Lucie Bednárová is acknowledged for the CD spectra measurements and Karel Musil for the introductory synthetic studies.
These authors contributed equally to this work.
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201108307