金金屬催化環化連烯烴取代酯類與苯並異噁唑經由一、二號位連烯烴遷移

Gold-catalyzed Annulations between Allenyl Esters and Benzisoxazoles Involving a 1,2-Allene Shift

譚國成(Kuo-Chen Tan)

指導教授 ： 劉瑞雄

國立清華大學/理學院/化學系所/碩士(2019年)

摘要

利用4-甲氧基-1,2-二烯-5-炔與苯並異噁唑進行金催化[4 + 1]環化反應如圖所示。環化機構中藉由形成氮烯、α-亞胺金碳烯和一、二號位連烯烴遷移形成(pyrrol-2-yl)methylgold 中間體。這些連烯烴取代的酯類基質，其金金屬中間體能進一步形成烯醇，進行羥醛反應，形成有用的pyrrolo[1,2-a]quinoline 衍生物。

關鍵字

金催化 ； 連烯烴 ； 苯並異噁唑

並列摘要

Gold-catalyzed [4+1]-annulations of 4-methoxy-1,2-dienyl-5-ynes with benzisoxazole are described. The mechanism of these annulations involves nitrene formation of α-imino gold carbenes that undergo a 1,2-allene shift to form (pyrrol-2-yl)methylgold intermediates. With allenyl ester substrates, these gold intermediates become enolate species to enable intramolecular aldol reactions to form useful pyrrolo[1,2-a]quinoline derivatives.

並列關鍵字

Gold-catalyzed ； Allene ； Benzisoxazole

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