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 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.