Enantioselective Synthesis of [9]- and [11]Helicene-like Molecules: Double Intramolecular [2+2+2] Cycloaddition

Authors

  • Yuki Kimura,

    1. Department of Applied Chemistry, Graduate School of Engineering, Tokyo University of Agriculture and Technology, Koganei, Tokyo 184-8588 (Japan)
    Search for more papers by this author
  • Naohiro Fukawa,

    1. Department of Applied Chemistry, Graduate School of Engineering, Tokyo University of Agriculture and Technology, Koganei, Tokyo 184-8588 (Japan)
    Search for more papers by this author
  • Yuta Miyauchi,

    1. Department of Applied Chemistry, Graduate School of Engineering, Tokyo University of Agriculture and Technology, Koganei, Tokyo 184-8588 (Japan)
    Search for more papers by this author
  • Prof. Dr. Keiichi Noguchi,

    1. Instrumentation Analysis Center, Tokyo University of Agriculture and Technology, Koganei, Tokyo 184-8588 (Japan)
    Search for more papers by this author
  • Prof. Dr. Ken Tanaka

    Corresponding author
    1. Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, Ookayama, Meguro-ku, Tokyo 152-8550 (Japan) http://www.tuat.ac.jp/∼tanaka-k/
    2. Department of Applied Chemistry, Graduate School of Engineering, Tokyo University of Agriculture and Technology, Koganei, Tokyo 184-8588 (Japan)
    3. Japan Science and Technology Agency, ACT-C, 4-1-8 Honcho, Kawaguchi, Saitama, 332-0012 (Japan)
    • Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, Ookayama, Meguro-ku, Tokyo 152-8550 (Japan) http://www.tuat.ac.jp/∼tanaka-k/===

    Search for more papers by this author

  • This work was supported partly by ACT-C from Japan Science and Technology Agency (Japan) and a Grant-in-Aid for Scientific Research (No. 20675002) from the Ministry of Education, Culture, Sports, Science and Technology (Japan). We are grateful to Takasago International Corporation for the gift of segphos and Umicore for generous support in supplying the rhodium complex.

Abstract

The enantioselective synthesis of completely ortho-fused [9]- and [11]helicene-like molecules has been achieved through a rhodium-mediated, intramolecular, double [2+2+2] cycloaddition of phenol- or 2-naphthol-linked hexaynes. Crystal structures and photophysical properties of these [9]- and [11]helicene-like molecules have also been disclosed.

Ancillary