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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)
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  • Misaki Taniguchi,

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

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

    1. Department of Frontier Materials&Department of Nanopharmaceutical Science, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan)
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  • Prof. Dr. Tomohiro Ozawa,

    1. Department of Frontier Materials&Department of Nanopharmaceutical Science, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan)
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  • Prof. Dr. Hideki Masuda,

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

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  • 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

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Six transformations, one pot: Various di- and trisubstituted vinyl triflones, as well as several heteroaryl triflones, were stereoselectively synthesized from easily accessible gem-dibromovinyl substrates (see scheme, Boc=tert-butoxycarbonyl). The highlights of this synthetic method lie in the remote O→Cvinyl or N→Cvinyl triflyl migrations and the one-pot, three-step protocol.

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