Premium
[2+2+2] Cycloisomerisation of Aromatic Cyanodiynes in the Synthesis of Pyridohelicenes and Their Analogues
Author(s) -
Klívar Jiří,
Jančařík Andrej,
Šaman David,
Pohl Radek,
Fiedler Pavel,
Bednárová Lucie,
Starý Ivo,
Stará Irena G.
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201602747
Subject(s) - helicene , enantiopure drug , intramolecular force , chemistry , pyridine , folding (dsp implementation) , stereochemistry , molecule , substrate (aquarium) , enantioselective synthesis , medicinal chemistry , organic chemistry , catalysis , oceanography , engineering , geology , electrical engineering
We have developed a methodology for the synthesis of pyridohelicenes and their analogues based on the Ni 0 ‐, Co I ‐ or Rh I ‐mediated intramolecular [2+2+2] cycloisomerisation of cyanodiynes. It allows for folding the linear precursors into the corresponding helical backbones comprising the newly formed pyridine unit in their central part. Along with racemic pyrido[ n ]helicenes ( n =5,6,7) and their derivatives, both enantio‐ and diastereomerically pure pyrido[ n ]helicene‐like molecules ( n =5,6) were prepared by employing the chiral substrate‐controlled cyclisation of the corresponding enantiopure cyanodiynes.