Dynamic Kinetic Resolution of rac-2-Hydroxy-1-indanone by using a Heterogeneous Ru(OH)3/Al2O3 Racemization Catalyst and Lipase

Authors

  • Otto Långvik,

    1. Laboratory of Organic Chemistry, Åbo Akademi University, Biskopsgatan 8, FIN-20500, Åbo (Finland), Fax: (+358) 2-2154866
    2. Graduate School of Materials Research, Åbo Akademi University, Porthansgatan 3-5, FIN-20500, Åbo (Finland)
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  • Tiina Saloranta,

    1. Laboratory of Organic Chemistry, Åbo Akademi University, Biskopsgatan 8, FIN-20500, Åbo (Finland), Fax: (+358) 2-2154866
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  • Alexey Kirilin,

    1. Laboratory of Industrial Chemistry and Reaction Engineering, Process Chemistry Centre, Åbo Akademi University, Biskopsgatan 8, FIN-20500 Åbo (Finland)
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  • Dr. Arto Liljeblad,

    1. Pharmacology, Drug Development and Therapeutics/, Laboratory of Synthetic Drug Chemistry, University of Turku, Lemminkäisenkatu 5 C, FIN-20250 Turku (Finland)
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  • Dr. Päivi Mäki-Arvela,

    1. Laboratory of Industrial Chemistry and Reaction Engineering, Process Chemistry Centre, Åbo Akademi University, Biskopsgatan 8, FIN-20500 Åbo (Finland)
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  • Prof. Liisa T. Kanerva,

    1. Pharmacology, Drug Development and Therapeutics/, Laboratory of Synthetic Drug Chemistry, University of Turku, Lemminkäisenkatu 5 C, FIN-20250 Turku (Finland)
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  • Prof. Dmitry Yu. Murzin,

    Corresponding author
    1. Laboratory of Industrial Chemistry and Reaction Engineering, Process Chemistry Centre, Åbo Akademi University, Biskopsgatan 8, FIN-20500 Åbo (Finland)
    • Laboratory of Industrial Chemistry and Reaction Engineering, Process Chemistry Centre, Åbo Akademi University, Biskopsgatan 8, FIN-20500 Åbo (Finland)
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  • Prof. Reko Leino

    Corresponding author
    1. Laboratory of Organic Chemistry, Åbo Akademi University, Biskopsgatan 8, FIN-20500, Åbo (Finland), Fax: (+358) 2-2154866
    • Laboratory of Organic Chemistry, Åbo Akademi University, Biskopsgatan 8, FIN-20500, Åbo (Finland), Fax: (+358) 2-2154866
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Abstract

Kinetic resolution and dynamic kinetic resolution, in particular, provide practical tools for synthesis of enantiomerically pure compounds. In the present work, the resolution of rac-2-hydroxy-1-indanone and racemization of (S)-2-hydroxy-1-indanone were investigated. Immobilized lipase AK (Pseudomonas fluorescens) was found as the best enzyme catalyst for kinetic resolution and ruthenium supported on Al2O3 as a potential heterogeneous catalyst for racemization of the starting material. By combining the two reactions, a simple dynamic kinetic resolution of rac-2-hydroxy-1-indanone producing (R)-1-oxo-indan-2-yl butanoate was developed. Under optimal conditions, the product was obtained in 92 % ee at approximately 90 % conversion.

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