Asymmetric Transfer Hydrogenation of (<i>E</i>)-2-[1,2,6,7-Tetrahydro-8<i>H</i>-indeno[5,4-<i>b</i>]furan-8-ylidene]acetaldehyde Using Polymer-Supported Chiral Pyrrolidine Catalyst

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  • Naoki Haraguchi
    Department of Applied Chemistry and Life Science, Toyohashi University of Technology, Tempaku-cho, Toyohashi, Aichi 441-8580 , Japan
  • Rina Watanabe
    Department of Applied Chemistry and Life Science, Toyohashi University of Technology, Tempaku-cho, Toyohashi, Aichi 441-8580 , Japan
  • Shinichi Itsuno
    Department of Applied Chemistry and Life Science, Toyohashi University of Technology, Tempaku-cho, Toyohashi, Aichi 441-8580 , Japan
  • Hidenori Ochiai
    Pharma & Supplemental Nutrition Solutions Vehicle, Pharma Business Division, Kaneka Corporation, 1-8 Miyamae-cho, Takasago-cho, Takasago, Hyogo 676-8688 , Japan
  • Akira Nishiyama
    Pharma & Supplemental Nutrition Solutions Vehicle, Pharma Business Division, Kaneka Corporation, 1-8 Miyamae-cho, Takasago-cho, Takasago, Hyogo 676-8688 , Japan

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<jats:title>Abstract</jats:title> <jats:p>The asymmetric transfer hydrogenation of α,β-unsaturated aldehyde with Hantzsch ester catalyzed by polymer-supported chiral pyrrolidine organocatalyst was achieved. The effects of the pyrrolidine substituents and linkage configuration on the catalytic performance were examined in detail. We found that the polymer-supported cis-type chiral pyrrolidine organocatalysts showed high enantioselectivities (up to 99.9%) compared with the corresponding trans analogs and monomers in the reaction. The recovered catalyst was reused without any loss of the catalytic activity.</jats:p>

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