银催化的环庚三烯酮与高丝氨酸内酯衍生的亚甲胺叶立德的[6+3]环加成反应
首发时间:2016-03-31
摘要:本文报道了AgOAc/PPh3催化的环庚三烯酮与高丝氨酸内酯衍生的亚甲胺叶立德的[6+3]环加成反应。该反应具有操作简单、条件温和、官能团兼容性好的特点,能以中等到良好的产率和优异的非对映选择性得到具有三环结构的螺哌啶杂环化合物。利用此方法合成的目标产物结构均经过1H NMR、13C NMR、IR、HRMS 等数据确认,其相对构型得到了X-ray单晶衍射数据的确认。该反应有望在天然产物和生物活性分子合成中得到应用。
关键词: 环加成 环庚三烯酮 亚甲胺叶立德 高丝氨酸内酯 螺哌啶
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Ag-Catalyzed [6+3] Cycloaddition of Tropone with Homoserine Lactone Derived AzomethineYlides: Synthesis of Tricyclic Spiropiperidine
Abstract:Ag-catalyzed [6+3] cycloaddition of tropone with homoserine lactone derived azomethineylides has been achieved. The reaction works efficiently under mild conditions to give tricyclic spiropiperidine products in moderate to good yields with excellent diastereoselectivity. These products have been characterized by 1H NMR、13C NMR、IR and HRMS data. Their relative configuration was confirmed by X-ray crystallographic data. The reaction will find potential application in synthesis of natural products and biologically important compounds.
Keywords: cycloaddition tropone azomethineylide homoserine lactone spiropiperidine
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银催化的环庚三烯酮与高丝氨酸内酯衍生的亚甲胺叶立德的[6+3]环加成反应
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