Lipase-catalyzed kinetic resolution of 1-(2-Hydroxycyclohexyl)indoles in batch and continuous-flow systems

Péter Falus, Zoltán Boros, Péter Kovács, L. Poppe, József Nagy

Research output: Contribution to journalArticle

12 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)125-134
Number of pages10
JournalJournal of Flow Chemistry
Volume4
Issue number3
DOIs
Publication statusPublished - Sep 17 2014

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Indoles
Acylation
Enzyme kinetics
Lipases
Lipase
Kinetics
Cyclohexanols
Reaction rates
Productivity
Derivatives
Oxides
Acetates
Temperature
indole

Keywords

  • continuous-flow biotransformation
  • enantiomer selectivity
  • heterocyclic secondary alcohol
  • kinetic resolution
  • lipase
  • temperature effect

ASJC Scopus subject areas

  • Chemistry (miscellaneous)
  • Fluid Flow and Transfer Processes
  • Organic Chemistry

Cite this

Lipase-catalyzed kinetic resolution of 1-(2-Hydroxycyclohexyl)indoles in batch and continuous-flow systems. / Falus, Péter; Boros, Zoltán; Kovács, Péter; Poppe, L.; Nagy, József.

In: Journal of Flow Chemistry, Vol. 4, No. 3, 17.09.2014, p. 125-134.

Research output: Contribution to journalArticle

Falus, Péter ; Boros, Zoltán ; Kovács, Péter ; Poppe, L. ; Nagy, József. / Lipase-catalyzed kinetic resolution of 1-(2-Hydroxycyclohexyl)indoles in batch and continuous-flow systems. In: Journal of Flow Chemistry. 2014 ; Vol. 4, No. 3. pp. 125-134.
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