Synthesis of Hexahelicene and 1-Methoxyhexahelicene via Cycloisomerization of Biphenylyl-Naphthalene Derivatives

• Published in: Journal of organic chemistry Vol. 74; no. 8; pp. 3090 - 3093
• Main Authors: Storch, Jan, Sýkora, Jan, Čermák, Jan, Karban, Jindřich, Císařová, Ivana, Růžička, Aleš
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 17.04.2009; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Organic; Condensed benzenic and aromatic compounds; Exact sciences and technology; Noncondensed benzenic compounds; Organic chemistry; Physical Sciences; Preparations and properties; Science & Technology; ASYMMETRIC-SYNTHESIS; CIRCULAR-DICHROISM; ENANTIOSELECTIVE SYNTHESIS; HELICENE; RECOGNITION; CHIRAL DISCRIMINATION; RESOLUTION; EFFICIENT SYNTHESIS; PHENANTHRENE; CYCLIZATION; Catalytic reaction; Molecular assembly; Biphenyl derivatives; Platinum; Isomerization; Helicene; Cycloisomerization; Transition metal; Aromatic compound; Chemical synthesis; Naphthalene derivatives
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo900077j

The new approach provides nonphotochemical syntheses of helicenes based on the easy, convergent, and modular assembly of key biphenylyl-naphthalenes and their platinum-catalyzed double cycloisomerization. This sequence of reactions provides a synthetic route to helicenes in two steps from simply accessible building blocks. Furthermore, the method enables the introduction of substituents into the hexahelicene skeleton. The strategy developed is exemplified by the synthesis of 6,10-dimethylhexahelicene and 1-methoxy-6,10-dimethylhexahelicene.