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

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Zoltán BorosDepartment of Organic Chemistry and Technology, Budapest University of Technology and Economics, H-1111, Budapest, Műegyetem rkp. 3, Hungary
SynBiocat Ltd., H-1173 Budapest, Lázár, deák u, 4/1, Hungary

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

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László PoppeDepartment of Organic Chemistry and Technology, Budapest University of Technology and Economics, H-1111, Budapest, Műegyetem rkp. 3, Hungary
SynBiocat Ltd., H-1173 Budapest, Lázár, deák u, 4/1, Hungary

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József NagyDepartment of Organic Chemistry and Technology, Budapest University of Technology and Economics, H-1111, Budapest, Műegyetem rkp. 3, Hungary
SynBiocat Ltd., H-1173 Budapest, Lázár, deák u, 4/1, Hungary

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Abstract

The lipase catalyzed kinetic resolution of three trans-1-(2-hydroxycyclohexyl)-indoles in both batch and continuous-flow 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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Journal of Flow Chemistry
Language English
Size A4
Year of
Foundation
2011
Volumes
per Year
1
Issues
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4
Founder Áramlásos Kémiai Tudományos Társaság
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ISSN 2062-249X (Print)
ISSN 2063-0212 (Online)