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Collect. Czech. Chem. Commun. 2003, 68, 917-930
https://doi.org/10.1135/cccc20030917

Synthesis of Helicene Scaffolds via [2+2+2] Cycloisomerization of Aromatic Triynes

Irena G. Stará*, Ivo Starý*, Adrian Kollárovič, Filip Teplý, David Šaman and Pavel Fiedler

Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, 166 10 Prague 6, Czech Republic

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  • Fang Lei, Li Meng, Lin Wei-Bin, Shen Yun, Chen Chuan-Feng: Synthesis, Structures, and Photophysical Properties of Optically Stable 1,16-Diphenyl-3,14-diaryl-Substituted Tetrahydrobenzo[5]helicenediol Derivatives: Enantioselective Recognition toward Tryptophan Methyl Esters. J. Org. Chem. 2017, 82, 7402. <https://doi.org/10.1021/acs.joc.7b01087>
  • Wang Liang, Li Xuehu, Tao Hua, Zhou Xiang, Lu Xihong, Du Wenyue, Jiang Tingting, Xin Zhijun, Liang Jianping: Palladium-catalyzed intermolecular tandem cyclization reaction: a highly regioselective synthesis of functionalized 3H-spiro[isobenzofuran-1,3′-isochroman] scaffolds. Org. Biomol. Chem. 2017, 15, 2403. <https://doi.org/10.1039/C6OB02802K>
  • Roose Jesse, Achermann Stefan, Dumele Oliver, Diederich François: Electronically Connected [n]Helicenes: Synthesis and Chiroptical Properties of Enantiomerically Pure (E)‐1,2‐Di([6]helicen‐2‐yl)ethenes. Eur J Org Chem 2013, 2013, 3223. <https://doi.org/10.1002/ejoc.201300407>
  • Heller Barbara, Hapke Marko, Fischer Christine, Andronova Angelina, Starý Ivo, Stará Irena G.: Chiral cobaltI and nickel0 complexes in the synthesis of nonracemic helicenes through the enantioselective [2 + 2 + 2] cyclotrimerisation of alkynes. Journal of Organometallic Chemistry 2013, 723, 98. <https://doi.org/10.1016/j.jorganchem.2012.07.005>
  • Lin Wei, Dou Guo-Lan, Hu Ming-Hua, Cao Cheng-Pao, Huang Zhi-Bin, Shi Da-Qing: Facile, Efficient, and Diastereoselective Synthesis of Heterohelicene-like Molecules. Org. Lett. 2013, 15, 1238. <https://doi.org/10.1021/ol400154j>
  • Gingras Marc: One hundred years of helicene chemistry. Part 1: non-stereoselective syntheses of carbohelicenes. Chem. Soc. Rev. 2013, 42, 968. <https://doi.org/10.1039/C2CS35154D>
  • Shen Yun, Chen Chuan-Feng: Helicenes: Synthesis and Applications. Chem. Rev. 2012, 112, 1463. <https://doi.org/10.1021/cr200087r>
  • Pratap Ramendra, Kumar Abhinav, Pick Rigoberg, Hüch Volker, Ram Vishnu Ji: Metal-free synthesis of nitrile based partially reduced thia-and oxa-thia[5]helicenes: conformation and dynamics. RSC Adv. 2012, 2, 1557. <https://doi.org/10.1039/C1RA00824B>
  • Krausová Zuzana, Sehnal Petr, Bondzic Bojan P., Chercheja Serghei, Eilbracht Peter, Stará Irena G., Šaman David, Starý Ivo: Helicene‐Based Phosphite Ligands in Asymmetric Transition‐Metal Catalysis: Exploring Rh‐Catalyzed Hydroformylation and Ir‐Catalyzed Allylic Amination. Eur J Org Chem 2011, 2011, 3849. <https://doi.org/10.1002/ejoc.201100259>
  • Stará Irena G., Andronova Angelina, Kollárovič Adrian, Vyskočil Štěpán, Jugé Sylvain, Lloyd-Jones Guy C., Guiry Patrick J., Starý Ivo: Enantioselective [2+2+2] cycloisomerisation of alkynes in the synthesis of helicenes: The search for effective chiral ligands. Collect. Czech. Chem. Commun. 2011, 76, 2005. <https://doi.org/10.1135/cccc2011177>
  • Ho Joanne Hui Hui, Hodgson Richard, Wagler Jörg, Messerle Barbara Ann: Highly efficient Rh(i) and Ir(i) single and dual metal catalysed dihydroalkoxylation reactions of alkyne diols. Dalton Trans. 2010, 39, 4062. <https://doi.org/10.1039/b926773e>
  • Storch Jan, Sýkora Jan, Čermák Jan, Karban Jindřich, Císařová Ivana, Růžička Aleš: Synthesis of Hexahelicene and 1-Methoxyhexahelicene via Cycloisomerization of Biphenylyl-Naphthalene Derivatives. J. Org. Chem. 2009, 74, 3090. <https://doi.org/10.1021/jo900077j>
  • Perzyna Aurore, Zotto Christophe Dal, Durand Jean‐Olivier, Granier Michel, Smietana Michael, Melnyk Oleg, Stará Irena G., Starý Ivo, Klepetářová Blanka, Šaman David: Reaction of Isocyanate‐Functionalised Silicon Wafers with Complex Amino Compounds. Eur J Org Chem 2007, 2007, 4032. <https://doi.org/10.1002/ejoc.200700044>
  • Teplý Filip, Stará Irena G., Starý Ivo, Kollárovič Adrian, Luštinec Daniel, Krausová Zuzana, Šaman David, Fiedler Pavel: A Convenient Route to 2‐Hydroxy‐ and 2,15‐Dihydroxyhexahelicene. Eur J Org Chem 2007, 2007, 4244. <https://doi.org/10.1002/ejoc.200700381>
  • Kamikawa Ken, Takemoto Ippei, Takemoto Shin, Matsuzaka Hiroyuki: Synthesis of Helicenes Utilizing Palladium-Catalyzed Double C−H Arylation Reaction. J. Org. Chem. 2007, 72, 7406. <https://doi.org/10.1021/jo0711586>
  • Harrowven David C., Guy Ian L., Nanson Lana: Efficient Phenanthrene, Helicene, and Azahelicene Syntheses. Angewandte Chemie 2006, 118, 2300. <https://doi.org/10.1002/ange.200504287>
  • Harrowven David C., Guy Ian L., Nanson Lana: Efficient Phenanthrene, Helicene, and Azahelicene Syntheses. Angew Chem Int Ed 2006, 45, 2242. <https://doi.org/10.1002/anie.200504287>
  • Turek Pavel, Novák Petr, Pohl Radek, Hocek Michal, Kotora Martin: Preparation of Highly Substituted 6-Arylpurine Ribonucleosides by Ni-Catalyzed Cyclotrimerization. Scope of the Reaction. J. Org. Chem. 2006, 71, 8978. <https://doi.org/10.1021/jo061485y>
  • Novák Petr, Pohl Radek, Kotora Martin, Hocek Michal: Synthesis of C-Aryldeoxyribosides by [2 + 2 + 2]-Cyclotrimerization Catalyzed by Rh, Ni, Co, and Ru Complexes. Org. Lett. 2006, 8, 2051. <https://doi.org/10.1021/ol060454m>
  • Alexandrová Zuzana, Sehnal Petr, Stará Irena G., Starý Ivo, Šaman David, Urquhart Stephen G., Otero Edwige: Modified Synthesis of Heptahelicene and Its Resolution Into Single Enantiomers. Collect. Czech. Chem. Commun. 2006, 71, 1256. <https://doi.org/10.1135/cccc20061256>
  • Schneider Jochen F., Nieger Martin, Nättinen Kalle, Lewall Burhanshah, Niecke Edgar, Dötz Karl Heinz: Novel [6]‐ and [7]Helicene‐Like Quinones via Mono‐ and Bidirectional Chromium‐Templated Benzannulation of Bridged Binaphthyl Carbene Complexes. Eur J Org Chem 2005, 2005, 1541. <https://doi.org/10.1002/ejoc.200400800>
  • Carreño M. Carmen, González-López Marcos, Urbano Antonio: Efficient asymmetric synthesis of [7]helicene bisquinones. Chem. Commun. 2005, 611. <https://doi.org/10.1039/B413879A>
  • Turek Pavel, Kotora Martin, Tišlerová Iva, Hocek Michal, Votruba Ivan, Císařová Ivana: Cocyclotrimerization of 6-Alkynylpurines with α,ω-Diynes as a Novel Approach to Biologically Active 6-Arylpurines. J. Org. Chem. 2004, 69, 9224. <https://doi.org/10.1021/jo0486342>
  • Alexandrová Zuzana, Stará Irena G., Sehnal Petr, Teplý Filip, Starý Ivo, Šaman David, Fiedler Pavel: Synthetic Studies Toward Chiral Aromatic Triynes as Key Substrates for the Asymmetric Synthesis of Helicene-Like Molecules. Collect. Czech. Chem. Commun. 2004, 69, 2193. <https://doi.org/10.1135/cccc20042193>
  • Urbano Antonio: Neuere Entwicklungen in der Synthese Helicen‐artiger Moleküle. Angewandte Chemie 2003, 115, 4116. <https://doi.org/10.1002/ange.200301667>
  • Urbano Antonio: Recent Developments in the Synthesis of Helicene‐Like Molecules. Angew Chem Int Ed 2003, 42, 3986. <https://doi.org/10.1002/anie.200301667>
  • Stara Irena G., Stary Ivo, Kollarovic Adrian, Teply Filip, Saman David, Fiedler Pavel: Synthesis of Helicene Scaffolds via [2 + 2 + 2] Cycloisomerization of Aromatic Triynes. ChemInform 2003, 34. <https://doi.org/10.1002/chin.200334087>
  • Paruch Kamil, Vyklický Libor, Wang David Zhigang, Katz Thomas J., Incarvito Christopher, Zakharov Lev, Rheingold Arnold L.: Functionalizations of [6]- and [7]Helicenes at Their Most Sterically Hindered Positions. J. Org. Chem. 2003, 68, 8539. <https://doi.org/10.1021/jo035057t>