Get access

Stereoselective Synthesis of Vinyl Triflones and Heteroaryl Triflones through Anionic O→Cvinyl and N→Cvinyl Trifluoromethanesulfonyl Migration Reactions

Authors

  • Dr. Xiu-Hua Xu,

    1. Department of Frontier Materials&Department of Nanopharmaceutical Science, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan)
    Search for more papers by this author
  • Misaki Taniguchi,

    1. Department of Frontier Materials&Department of Nanopharmaceutical Science, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan)
    Search for more papers by this author
  • Xin Wang,

    1. Department of Frontier Materials&Department of Nanopharmaceutical Science, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan)
    Search for more papers by this author
  • Etsuko Tokunaga,

    1. Department of Frontier Materials&Department of Nanopharmaceutical Science, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan)
    Search for more papers by this author
  • Prof. Dr. Tomohiro Ozawa,

    1. Department of Frontier Materials&Department of Nanopharmaceutical Science, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan)
    Search for more papers by this author
  • Prof. Dr. Hideki Masuda,

    1. Department of Frontier Materials&Department of Nanopharmaceutical Science, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan)
    Search for more papers by this author
  • Prof. Dr. Norio Shibata

    Corresponding author
    1. Department of Frontier Materials&Department of Nanopharmaceutical Science, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan)
    • Department of Frontier Materials&Department of Nanopharmaceutical Science, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan)

    Search for more papers by this author

  • This study was financially supported in part by the Platform for Drug Discovery, Informatics, and Structural Life Science from the Ministry of Education, Culture, Sports, Science and Technology (Japan), by Grants-in-Aid for Scientific Research from MEXT (Ministry of Education, Culture, Sports, Science and Technology) (24105513, Project No. 2304: Advanced Molecular Transformation by Organocatalysts), and JST (ACT-C: Creation of Advanced Catalytic Transformation for the Sustainable Manufacturing at Low Energy, Low Environmental Load). X.H.X. thanks JSPS Postdoctoral Fellowship Program for Foreign Researchers. T.O. and H.M. conducted X-ray crystallographic analysis of 5 a.

Abstract

original image

Sechs Umwandlungen, ein Gefäß: Verschiedene di- und trisubstituierte Vinyltriflone sowie mehrere Heteroaryltriflone wurden ausgehend von leicht zugänglichen gem-Dibromvinylsubstraten selektiv synthetisiert (siehe Schema, Boc=tert-Butoxycarbonyl). Highlights dieser Methode sind die weiten O→CVinyl- oder N→CVinyl-Triflylwanderungen und die dreistufige Synthese in nur einem Reaktionsgefäß.

Ancillary