Click reaction-aided enzymatic kinetic resolution of secondary alcoholsElectronic supplementary information (ESI) available: Protocols for chemical synthesis and spectral characterization of involved compounds, copper(i) source screening for the click reaction, optimization studies of EKR and chromatographic chiral separation conditions and chromatograms. See DOI: 10.1039/c8re00091c
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 t...
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Sprache: | eng |
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Zusammenfassung: | 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.
A new, efficient lipase-mediated kinetic resolution-click-reaction-based procedure is presented for the production of both enantiomers of various 1-(hetero)aromatic ethanols. |
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ISSN: | 2058-9883 |
DOI: | 10.1039/c8re00091c |