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

0323582 - ÚCHP 2009 RIV US eng J - Journal Article
Storch, Jan - Sýkora, Jan - Čermák, Jan - Karban, Jindřich - Císařová, I. - Růžička, A.
Synthesis of Hexahelicene and 1-Methoxyhexahelicene via Cycloisomerization of Biphenylyl-Naphthalene Derivatives.
[Syntéza hexahelicenu a 1-methoxyhexahelicenu cykloizomerací bifenyly-naftalenů.]
Journal of Organic Chemistry. Roč. 74, č. 8 (2009), s. 3090-3093. ISSN 0022-3263. E-ISSN 1520-6904
R&D Projects: GA ČR GA203/06/0738; GA MŠMT(CZ) LC06070
Institutional research plan: CEZ:AV0Z40720504
Keywords : helicenes * cycloisomerization * chiral
Subject RIV: CC - Organic Chemistry
Impact factor: 4.219, year: 2009

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.

Nový nefotochemický přístup k syntéze helicenů, založený na konvergentním a modulárním sestavovaní klíčových bifenylyl-naftalenů. Jejich dvojnásobná cyklozimerace poskytuje 6,10-dimethylhexahelicen a 1-methoxy-6,10-dimethylhexahelicen.
Permanent Link: http://hdl.handle.net/11104/0171495