Get access

Enantioselective Isomerization of Primary Allylic Alcohols into Chiral Aldehydes with the tol-binap/dbapen/Ruthenium(II) Catalyst

Authors

  • Prof. Dr. Noriyoshi Arai,

    1. Division of Chemical Process Engineering and Frontier Chemistry Center, Faculty of Engineering, Hokkaido University, Sapporo, Hokkaido 060-8628 (Japan)
    Search for more papers by this author
  • Keisuke Sato,

    1. Division of Chemical Process Engineering and Frontier Chemistry Center, Faculty of Engineering, Hokkaido University, Sapporo, Hokkaido 060-8628 (Japan)
    Search for more papers by this author
  • Keita Azuma,

    1. Division of Chemical Process Engineering and Frontier Chemistry Center, Faculty of Engineering, Hokkaido University, Sapporo, Hokkaido 060-8628 (Japan)
    Search for more papers by this author
  • Prof. Dr. Takeshi Ohkuma

    Corresponding author
    1. Division of Chemical Process Engineering and Frontier Chemistry Center, Faculty of Engineering, Hokkaido University, Sapporo, Hokkaido 060-8628 (Japan)
    • Division of Chemical Process Engineering and Frontier Chemistry Center, Faculty of Engineering, Hokkaido University, Sapporo, Hokkaido 060-8628 (Japan)
    Search for more papers by this author

  • This work was supported by a Grant-in-Aid from the Japan Society for the Promotion of Science (JSPS) (No. 24350042) and by a MEXT (Japan) program, “Strategic Molecular and Materials Chemistry through Innovative Coupling Reactions,” of Hokkaido University. dbapen=2-dibutylamino-1-phenylethylamine, tol-binap=2,2′-bis(di-4-tolylphosphanyl)-1,1′-binaphthyl.

Abstract

original image

Efficient isomerization: The title reaction was catalyzed by the [RuCl2{(S)-tol-binap}{(R)-dbapen}]/KOH system in ethanol at 25 °C (see scheme). A series of E- and Z-configured aromatic and aliphatic allylic alcohols, including a simple primary alkyl-substituted compound (E)-3-methyl-2-hepten-1-ol, were transformed into the chiral aldehydes with at least 99 % ee. dbapen=2-dibutylamino-1-phenylethylamine, tol-binap=2,2′-bis(di-4-tolylphosphanyl)-1,1′-binaphthyl.

Get access to the full text of this article

Ancillary