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Copper‐Catalyzed Synthesis of α‐Trifluoromethylacrylates from Trifluoroborylacrylates via Stereoretentive Radical Trifluoromethylation
Advanced Synthesis & Catalysis ( IF 5.4 ) Pub Date : 2020-10-01 , DOI: 10.1002/adsc.202000937
Swetha Jos 1 , Webster Santos 1
Affiliation  

We report the synthesis of α‐trifluoromethylacrylates from α‐trifluoroborylacrylates via a stereoretentive radical trifluoromethylation with inexpensive reagents NaSO2CF3 and TBHP at room temperature. Under these conditions, a wide substrate scope afforded the (E)‐diastereomer exclusively in moderate to good yield. The utility of the reaction products is demonstrated in the synthesis of phenyl‐4H‐pyran, a potent and selective class of IKCa channel blockers.

中文翻译:

立体定向自由基三氟甲基化反应由铜催化丙烯酸三氟硼基酯合成α-三氟甲基丙烯酸酯

我们报告了在室温下通过廉价的NaSO 2 CF 3和TBHP试剂通过立体保持性自由基三氟甲基化反应从α-三氟硼基丙烯酸酯合成α-三氟甲基丙烯酸酯。在这些条件下,较宽的底物范围仅能以中等至良好的产率提供(E)-非对映异构体。该反应产物的效用在苯基-4 H-吡喃的合成中得到了证明,苯基-4 H-吡喃是一种强效且选择性的IKCa通道阻滞剂。
更新日期:2020-10-01
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