A Mesoporous-Silica-Immobilized Oxovanadium Cocatalyst for the Lipase-Catalyzed Dynamic Kinetic Resolution of Racemic Alcohols

Authors

  • Dr. Masahiro Egi,

    1. School of Pharmaceutical Sciences, University of Shizuoka, 52-1, Yada, Suruga-ku, Shizuoka, Shizuoka 422-8526 (Japan)
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  • Koji Sugiyama,

    1. School of Pharmaceutical Sciences, University of Shizuoka, 52-1, Yada, Suruga-ku, Shizuoka, Shizuoka 422-8526 (Japan)
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  • Moriaki Saneto,

    1. School of Pharmaceutical Sciences, University of Shizuoka, 52-1, Yada, Suruga-ku, Shizuoka, Shizuoka 422-8526 (Japan)
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  • Ryosuke Hanada,

    1. School of Pharmaceutical Sciences, University of Shizuoka, 52-1, Yada, Suruga-ku, Shizuoka, Shizuoka 422-8526 (Japan)
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  • Dr. Katsuya Kato,

    1. National Institute of Advanced Industrial Science and Technology (AIST), 2266-98 Anagahora, Shimo-shidami, Moriyama-ku, Nagoya, Aichi 463-8560 (Japan)
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  • Prof. Dr. Shuji Akai

    Corresponding author
    1. School of Pharmaceutical Sciences, University of Shizuoka, 52-1, Yada, Suruga-ku, Shizuoka, Shizuoka 422-8526 (Japan)
    • School of Pharmaceutical Sciences, University of Shizuoka, 52-1, Yada, Suruga-ku, Shizuoka, Shizuoka 422-8526 (Japan)===

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  • We are grateful to Prof. Hironao Sajiki of Gifu Pharmaceutical University (Japan) for his useful advice in clarifying the structure of V-MPS. This work was supported by a Grant-in-Aid for Scientific Research on Innovative Areas “Organic Synthesis Based on Reaction Integration” and a Grant-in-Aid for Scientific Research (B). We acknowledge Amano Enzyme, Inc. and Roche Diagnostics K.K. for supplying the lipases, and Taiyo Kagaku Co. Ltd. and Fuji Silysia, Chemical Ltd. for providing MPS and MacroPSs. We are also grateful to Prof. Masahiro Sakata and Dr. Satoshi Mitsunobu of the University of Shizuoka (Japan) and the N.E. Chemcat Corporation for measuring ICP, and to JEOL for measuring XPS.

Abstract

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V for resolution: A new oxovanadium catalyst (V-MPS; see scheme) immobilized in the pores of mesoporous silica has been developed. The combined use of V-MPS and lipases achieved the dynamic kinetic resolution of a wide range of racemic alcohols (1 or 2) to produce optically active esters 3 in high chemical and optical yields. The paired catalysts retained high catalytic activity when reused up to six times.

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