Catalytic Ugi-Type Condensation of 伪-Isocyanoacetamide and Chiral Cyclic Imine: Access to Asymmetric Construction of Several Heterocycles

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• 作者：Liang Xia ; Sheng Li ; Ruijiao Chen ; Kai Liu ; Xiaochuan Chen
• 刊名：The Journal of Organic Chemistry
• 出版年：2013
• 出版时间：April 5, 2013
• 年：2013
• 卷：78
• 期：7
• 页码：3120-3131
• 全文大小：422K
• 年卷期：v.78,no.7(April 5, 2013)
• ISSN：1520-6904

文摘

Several novel heterocycles have been constructed asymmetrically on the basis of a catalytic Ugi-type condensation of 伪-isocyanoacetamide and chiral cyclic imine. The combination of phenylphosphilic acid and trifluoroethanol is exploited to promote an Ugi-type reaction with 伪-isocyanoacetamide for the first time. By means of this reaction, chiral 3-oxazolyl morpholin-2-one/piperazin-2-one derivatives are synthesized with high yields and excellent stereoselectivities. As electron-rich azadienes, these condensation products are further transformed to fused tricyclic frameworks by treatment with appropriate dienophiles such as maleic anhydride and unsaturated acyl chlorides via domino processes. Moreover, a one-pot, three-component synthesis of the chiral tricyclic frameworks from isocyanoacetamide, imine, and maleic anhydride is also feasible.