Synthesis and stereochemical behavior of a new chiral oxa[7]heterohelicene

Ryo Irie, Akihiro Tanoue, Suguru Urakawa, Tatsushi Imahori, Kazunobu Igawa, Taisuke Matsumoto, Katsuhiko Tomooka, Shinsuke Kikuta, Tatsuya Uchida, Tsutomu Katsuki

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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.

Original languageEnglish
Pages (from-to)1343-1345
Number of pages3
JournalChemistry Letters
Volume40
Issue number12
DOIs
Publication statusPublished - 2011

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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    Irie, R., Tanoue, A., Urakawa, S., Imahori, T., Igawa, K., Matsumoto, T., Tomooka, K., Kikuta, S., Uchida, T., & Katsuki, T. (2011). Synthesis and stereochemical behavior of a new chiral oxa[7]heterohelicene. Chemistry Letters, 40(12), 1343-1345. https://doi.org/10.1246/cl.2011.1343