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.

中文翻译：

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单击反应辅助仲醇的酶促动力学拆分†

提出了一种新型高效的脂肪酶介导的动力学拆分（KR）-点击反应为基础的程序，用于通过2-（prop-2-yn-1）的酶促酰化反应生产各种1-（杂）芳族乙醇的两种对映异构体。 -酰氧基）乙酰基酯。点击反应为基础的原位（的衍生化- [R ）在KR步骤启用容易和有效分离从反应对映体产生-2-（丙-2-炔-1-基氧基）乙酸甲酯将衍生的（- [R ）-酯通过简单的萃取和从反应混合物中调节pH值来调节（S）醇。轻度和有效的衍生（R）酯的酶促乙醇化几乎可以定量回收（R）。）-酒精，对映体纯度没有可检测到的降低。该方法可以从各种1-（杂）芳族乙醇的外消旋物中提供几乎定量的两种对映体，而无需色谱分离KR产物。