Get access

Asymmetric Carboselenenylation Reaction of Alkenes with Aromatic Compounds

Authors

  • Kazuki Okamoto,

    1. Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto, 615-8510, Japan, Fax: (+81) 75-383-2517
    Search for more papers by this author
  • Yoshiaki Nishibayashi Dr.,

    1. Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto, 615-8510, Japan, Fax: (+81) 75-383-2517
    2. Current address: Institute of Engineering Innovation, School of Engineering, The University of Tokyo, Yayoi, Bunkyo-ku, Tokyo, 113-8656, Japan, Fax: (+81) 35-841-1175
    Search for more papers by this author
  • Sakae Uemura Prof. Emeritus Dr.,

    1. Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto, 615-8510, Japan, Fax: (+81) 75-383-2517
    Search for more papers by this author
  • Akio Toshimitsu Prof. Dr.

    1. International Innovation Center, Kyoto University, Sakyo-ku, Kyoto, 606-8501, Japan, Fax: (+81) 75-753-9174
    Search for more papers by this author

  • This work was supported by a Grant-in-Aid for Scientific Research for Young Scientists (A) (No. 15 685 006) to Y.N. from the Ministry of Education, Culture, Sports, Science, and Technology, Japan.

Abstract

original image

High diastereoselectivity is attained in the carboselenenylation reaction of simple alkenes with aromatic compounds by using a C2-symmetric areneselenenyl triflate (see scheme). This asymmetric Friedel–Crafts-type reaction is a convenient procedure for the preparation of chiral hydrocarbons bearing an aryl moiety at the stereogenic carbon atom. Tf=trifluoromethanesulfonyl; M.S.=molecular sieves.

Ancillary