Click reaction-aided enzymatic kinetic resolution of secondary alcohols

Mǎdǎlina Elena Moisǎ, L. Poppe, Cristian Andrei Gal, László Csaba Bencze, Florin Dan Irimie, Csaba Paizs, Francisc Peter, Monica Ioana Toşa

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

A new and efficient lipase-mediated kinetic resolution (KR)-click-reaction-based procedure is presented for the production of both enantiomers of various 1-(hetero)aromatic ethanols applying enzymatic acylation with 2-(prop-2-yn-1-yloxy)acetyl esters. Click-reaction-based in situ derivatization of the (R)-2-(prop-2-yn-1-yloxy)acetate produced from the reacting enantiomer in the KR step enabled facile and efficient separation of the derivatized (R)-ester and the (S)-alcohol by simple extractions and pH adjustments from the reaction mixture. A mild and efficient enzymatic ethanolysis of the derivatized (R)-ester allowed almost quantitative recovery of the (R)-alcohol without a detectable decrease in enantiopurity. The process could provide, from racemates of various 1-(hetero)aromatic ethanols, almost quantitatively both enantiomers without chromatographic separation of the KR products.

Original languageEnglish
Pages (from-to)790-798
Number of pages9
JournalReaction Chemistry and Engineering
Volume3
Issue number5
DOIs
Publication statusPublished - Oct 1 2018

ASJC Scopus subject areas

  • Catalysis
  • Chemistry (miscellaneous)
  • Chemical Engineering (miscellaneous)
  • Process Chemistry and Technology
  • Fluid Flow and Transfer Processes

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  • Cite this

    Moisǎ, M. E., Poppe, L., Gal, C. A., Bencze, L. C., Irimie, F. D., Paizs, C., Peter, F., & Toşa, M. I. (2018). Click reaction-aided enzymatic kinetic resolution of secondary alcohols. Reaction Chemistry and Engineering, 3(5), 790-798. https://doi.org/10.1039/c8re00091c