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Enzyme Promiscuity as a Remedy for the Common Problems with Knoevenagel Condensation
Chemistry - A European Journal ( IF 3.9 ) Pub Date : 2019-07-01 , DOI: 10.1002/chem.201901491 Dominik Koszelewski 1 , Ryszard Ostaszewski 1
Chemistry - A European Journal ( IF 3.9 ) Pub Date : 2019-07-01 , DOI: 10.1002/chem.201901491 Dominik Koszelewski 1 , Ryszard Ostaszewski 1
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A new protocol based on lipase‐catalyzed tandem reaction toward α,β‐enones/enoesters is presented. For the synthesis of the desired products the tandem process based on enzyme‐catalyzed hydrolysis and Knoevenagel reaction starting from enol acetates and aldehyde is developed. The relevant impact of the reaction conditions including organic solvent, enzyme type, and temperature on the course of the reaction was revealed. It was shown that controllable release of the active methylene compound from the corresponding enol carboxylate ensured by enzymatic reaction diminishes significantly the formation of the unwanted co‐products. Furthermore, this protocol was extended by including a second tandem chemoenzymatic transformation engaging various aldehyde precursors. After a careful optimization of the reaction conditions, the target products were obtained with yields up to 86 % and with excellent E/Z‐selectivity.
中文翻译：
酶混杂作为补救Knoevenagel冷凝常见问题的方法
提出了一种基于脂肪酶对α，β-烯醇/烯酸酯的串联反应的新方案。为了合成所需产物，开发了基于酶催化水解和从烯醇乙酸酯和醛开始的Knoevenagel反应的串联方法。揭示了反应条件（包括有机溶剂，酶类型和温度）对反应过程的相关影响。结果表明，通过酶促反应确保活性亚甲基化合物从相应的烯醇羧酸盐中的可控释放大大减少了不需要的副产物的形成。此外，通过包括与各种醛前体结合的第二串联化学酶转化来扩展该方案。在仔细优化反应条件后，E / Z选择性。
更新日期：2019-07-01
中文翻译：
酶混杂作为补救Knoevenagel冷凝常见问题的方法
提出了一种基于脂肪酶对α，β-烯醇/烯酸酯的串联反应的新方案。为了合成所需产物，开发了基于酶催化水解和从烯醇乙酸酯和醛开始的Knoevenagel反应的串联方法。揭示了反应条件（包括有机溶剂，酶类型和温度）对反应过程的相关影响。结果表明，通过酶促反应确保活性亚甲基化合物从相应的烯醇羧酸盐中的可控释放大大减少了不需要的副产物的形成。此外，通过包括与各种醛前体结合的第二串联化学酶转化来扩展该方案。在仔细优化反应条件后，E / Z选择性。
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