Synthesis and Stereochemical Behavior of a New Chiral Oxa[7]heterohelicene

• Ryo Irie

  Department of Chemistry, Graduate School of Science and Technology, Kumamoto University

• Akihiro Tanoue

  Department of Chemistry, Graduate School of Science and Technology, Kumamoto University

• Suguru Urakawa

  Department of Chemistry, Graduate School of Science and Technology, Kumamoto University

• Tatsushi Imahori

  Priority Organization for Innovation and Excellence, Kumamoto University

• Kazunobu Igawa

  Institute for Materials Chemistry and Engineering, Kyushu University

• Taisuke Matsumoto

  Institute for Materials Chemistry and Engineering, Kyushu University

• Katsuhiko Tomooka

  Institute for Materials Chemistry and Engineering, Kyushu University

• Shinsuke Kikuta

  Department of Chemistry, Graduate School of Sciences, Kyushu University

• Tatsuya Uchida

  Department of Chemistry, Graduate School of Sciences, Kyushu University

• Tsutomu Katsuki

  Department of Chemistry, Graduate School of Sciences, Kyushu University

Abstract

A new chiral oxa[7]heterohelicene 1b was synthesized by catalytic aerobic-oxidative tandem cyclization of the o-phenylene-linked bis(2-naphthol) derivative 3 with palladium acetate in dimethyl sulfoxide. Optical resolution of 1b was possible on chiral HPLC, but it was found stereochemically rather unstable at ambient temperature. Kinetic analysis and DFT calculation for the dynamics of racemization of 1b were also disclosed.

Journal

• Chemistry Letters

  Chemistry Letters 40 (12), 1343-1345, 2011-11-12

  Oxford University Press (OUP)

Keywords

• General Chemistry

Details

• CRID: 1360846644041638400
• NII Article ID: 130004426114
• DOI: 10.1246/cl.2011.1343
• ISSN: 13480715
• ISSN: 03667022
• Web Site: https://academic.oup.com/chemlett/article-pdf/40/12/1343/55606486/cl.2011.1343.pdf
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