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Synthesis of 2,4-Disubstituted Oxazoles by a Copper-Catalyzed [3+2] Annulation/Olefination Cascade between Amides and IIII/PV Hybrid Ylides
Synlett ( IF 1.7 ) Pub Date : 2023-11-06 , DOI: 10.1055/a-2185-0673
Xingchen Ye 1 , Zhaofeng Wang 1
Affiliation  

We report a novel and efficient method for oxazole synthesis through a copper-catalyzed [3+2] annulation/olefination cascade between readily available iodonium–phosphonium hybrid ylides and amides. An unprecedented α-phosphonium Cu carbenoid acts as the key intermediate. This method features excellent regioselectivity with mild reaction conditions and a broad substrate scope. Its synthetic utility is demonstrated by its application in late-stage functionalizations and the rapid synthesis of a chiral ligand based on an oxazole motif.



中文翻译:

通过酰胺和 IIII/PV 杂化叶立德之间的铜催化 [3+2] 成环/烯化级联合成 2,4-二取代恶唑

我们报告了一种新颖有效的恶唑合成方法,通过铜催化的[3+2]环化/烯化级联在容易获得的碘鏻杂化叶立德和酰胺之间进行。前所未有的 α-磷铜类胡萝卜素充当关键中间体。该方法具有优异的区域选择性、反应条件温和、底物范围广等特点。其合成效用通过其在后期功能化和基于恶唑基序的手性配体的快速合成中的应用得到证明。

更新日期:2023-11-07
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