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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

发表时间:2016-07-15  浏览量:4231  下载量:2290
全部作者: 吴阳,刘洪蕾,张磊,孙战虎,黄家兴,王敏,郭红超
作者单位: 中国农业大学理学院
摘 要: 报道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,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核磁共振谱(nuclear magnetic resonance,NMR)、红外光谱(infrared spectroscopy,IR)、高分辨质谱(high resolution mass spectrum,HRMS)等数据确认,其相对构型得到了单晶X-射线衍射数据的确认。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: 有机化学;环加成;环庚三烯酮;亚甲胺叶立德;高丝氨酸内酯;螺哌啶
Title: Ag-catalyzed [6+3] cycloaddition of tropone with homoserine lactone derived azomethine ylides: synthesis of tricyclic spiropiperidine
Author: WU Yang, LIU Honglei, ZHANG Lei, SUN Zhanhu, HUANG Jiaxing, WANG Min, GUO Hongchao
Organization: College of Science, China Agricultural University
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 nuclear magnetic resonance (NMR), infrared spectroscopy (IR) and high resolution mass spectrum (HRMS) data whose relative configurations were confirmed by X-ray crystallographic data. The reaction will find potential application in synthesis of natural products and biologically important compounds.
Key words: organic chemistry; cycloaddition; tropone; azomethine ylide; homoserine lactone; spiropiperidine
发表期数: 2016年7月第13期
引用格式: 吴阳,刘洪蕾,张磊,等. 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[J]. 中国科技论文在线精品论文,2016,9(13):1299-1307.
 
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