Enantioselective Helicene Synthesis by Rhodium-Catalyzed [2+2+2] Cycloadditions

The highly enantioselective synthesis of functionalized helicenes and helicene-like molecules have been achieved via rhodium-catalyzed [2+2+2] cycloaddition reactions. The rhodium-catalyzed enantioselective intramolecular [2+2+2] cycloaddition of 2-naphthol-linked triynes afforded [7]helicene-like m...

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Bibliographic Details
Published in:Bulletin of the Chemical Society of Japan 2015, Vol.88 (3), p.375-385
Main Authors: Tanaka, Ken, Kimura, Yuki, Murayama, Koichi
Format: Article
Language:English
Subjects:
Catalysis
Cycloaddition
Rhodium
Synthesis
Synthesis (chemistry)
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Summary:The highly enantioselective synthesis of functionalized helicenes and helicene-like molecules have been achieved via rhodium-catalyzed [2+2+2] cycloaddition reactions. The rhodium-catalyzed enantioselective intramolecular [2+2+2] cycloaddition of 2-naphthol-linked triynes afforded [7]helicene-like molecules in good yields and ee values. The more sterically encumbered reaction, the rhodium-catalyzed enantioselective double intramolecular [2+2+2] cycloaddition of a 2-naphthol-linked hexayne, also proceeded to give a [11]helicene-like molecule with high ee value, although the product yield was low. Not only intramolecular cycloaddition reactions but also intermolecular ones were accomplished by combinations of electron-rich tetraynes and electron-poor diynes to give [7]- and [9]helicene-like molecules and [7]helicenes in varying yields and ee values.
ISSN:0009-2673
1348-0634
DOI:10.1246/bcsj.20140291