期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 78, 期 7, 页码 3120-3131出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo4000702
关键词
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资金
- National Natural Science Foundation of China [20802045, 21172153, J1103315/J0104]
- National Basic Research Program of China (973 Program) [2012CB833200]
Several novel heterocycles have been constructed asymmetrically on the basis of a catalytic Ugi-type condensation of alpha-isocyanoacetamide and chiral cyclic imine. The combination of phenylphosphilic acid and trifluoroethanol is exploited to promote an Ugi-type reaction with alpha-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 stereo-selectivities. 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.
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