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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Bibliographic Details
Published in:Angewandte Chemie International Edition 2012-06, Vol.51 (24), p.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: Article
Language: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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201108307