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Lipase-Catalyzed Kinetic Resolution of 1-(2-Hydroxycyclohexyl)Indoles in Batch and Continuous-Flow Systems

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Abstract

The lipase catalyzed kinetic resolution of three trans-1-(2-hydroxycyclohexyl)-indoles in both batch and continuousflow systems is reported. Ring opening of cyclohexene oxide by the corresponding indole followed by enzymatic acylation with vinyl acetate resulted in novel, highly enantioenriched indole-substituted cyclohexanols and cyclohexyl acetates. The effect of the temperature on enantiomeric ratio (E) and productivity (specific reaction rate, rflow) in the continuous-flow mode acylation was studied at analytical scale in the 0–70 °C range. Preparative scale kinetic resolution of the three indole derivatives was performed in mixed continuous- and recirculation-flow mode resulting in almost complete conversion and good to excellent enantiomeric purity of the products.

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Authors and Affiliations

  1. Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, H-1111, Budapest, Műegyetem rkp. 3, Hungary

    Péter Falus, Zoltán Boros, László Poppe & József Nagy

  2. SynBiocat Ltd., H-1173, Budapest, Lázár, deák u 4/1, Hungary

    Zoltán Boros, László Poppe & József Nagy

  3. Research Centre for Natural Sciences, Institute of Organic Chemistry, Hungarian Academy of Sciences, H-1117, Budapest, Magyar tudósok körútja 2, Hungary

    Péter Kovács

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  1. Péter Falus
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  2. Zoltán Boros
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  3. Péter Kovács
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  4. László Poppe
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  5. József Nagy
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Correspondence to László Poppe or József Nagy.

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Falus, P., Boros, Z., Kovács, P. et al. Lipase-Catalyzed Kinetic Resolution of 1-(2-Hydroxycyclohexyl)Indoles in Batch and Continuous-Flow Systems. J Flow Chem 4, 125–134 (2014). https://doi.org/10.1556/JFC-D-14-00011

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