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Issue 5, 2018

Click reaction-aided enzymatic kinetic resolution of secondary alcohols

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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.

Graphical abstract: Click reaction-aided enzymatic kinetic resolution of secondary alcohols

Supplementary files

Article information


Submitted
28 May 2018
Accepted
20 Aug 2018
First published
20 Aug 2018

React. Chem. Eng., 2018,3, 790-798
Article type
Paper

Click reaction-aided enzymatic kinetic resolution of secondary alcohols

M. E. Moisă, L. Poppe, C. A. Gal, L. C. Bencze, F. D. Irimie, C. Paizs, F. Peter and M. I. Toşa, React. Chem. Eng., 2018, 3, 790 DOI: 10.1039/C8RE00091C

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