[2++2+2] Cycloisomerisation of Aromatic Cyanodiynes in the Synthesis of Pyridohelicenes and Their Analogues

0466272 - ÚOCHB 2017 RIV DE eng J - Journal Article
Klívar, Jiří - Jančařík, Andrej - Šaman, David - Pohl, Radek - Fiedler, Pavel - Bednárová, Lucie - Starý, Ivo - Stará, Irena G.
[2++2+2] Cycloisomerisation of Aromatic Cyanodiynes in the Synthesis of Pyridohelicenes and Their Analogues.
Chemistry - A European Journal. Roč. 22, č. 40 (2016), s. 14401-14405. ISSN 0947-6539. E-ISSN 1521-3765
R&D Projects: GA ČR(CZ) GA14-29667S
Institutional support: RVO:61388963
Keywords : aromatic compounds * chirality * helical structures * helicenes * heterocycles
Subject RIV: CC - Organic Chemistry
Impact factor: 5.317, year: 2016

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.
Permanent Link: http://hdl.handle.net/11104/0264611