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

详细信息    查看全文

• 作者：Jiří ; Klí ; var ; Andrej Jančaří ; k ; David Šaman ; Radek Pohl ; Pavel Fiedler ; Lucie Bedná ; rová ; Ivo Star&yacute ; and Irena G. Stará
• 刊名：Chemistry - A European Journal
• 出版年：2016
• 出版时间：September 26, 2016
• 年：2016
• 卷：22
• 期：40
• 页码：14401-14405
• 全文大小：586K
• ISSN：1521-3765

文摘

We have developed a methodology for the synthesis of pyridohelicenes and their analogues based on the Ni⁰-, 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.