Copper(I) Iodide-Catalyzed Cycloadditions of (1Z,4R*,5R*)-4-Benzamido-5-phenylpyrazolidin-3-on-1-azomethine Imines to Ethyl Propiolate
Copper(I) Iodide-Catalyzed Cycloadditions of (1Z,4R*,5R*)-4-Benzamido-5-phenylpyrazolidin-3-on-1-azomethine Imines to Ethyl Propiolate
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DOI：
10.1071/ch09074
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发表时间：
2009-01-01
影响因子：
1.1
通讯作者：
Svete, Jurij
中科院分区：
文献类型：
--
作者：
Pezdirc, Lidija;Stanovnik, Branko;Svete, Jurij
区域选择性碘化铜(i)催化手性吡唑烷-3-on-1-偶氮甲碱亚胺3a j 与丙炔酸乙酯4的环加成得到作为单一区域异构体的环加合物5a-h和5'i和5/5'j。就面选择性而言，环加合物5a-h和5'i以单一非对映异构体形式获得，而偶极子3j的反应选择性较低，得到5j和5'j比例为15:85的混合物。碘化铜(I)催化的丙炔酸乙酯4与偶氮甲碱亚胺3的环加成的立体选择性由5位上的立体定向苯基和1'-Ar残基上的邻位取代基控制。
Regioselective copper(i) iodide-catalyzed cycloadditions of chiral pyrazolidin-3-on-1-azomethine imines 3a j to ethyl propiolate 4 gave cycloadducts 5a-h and 5'i and 5/5'j as single regioisomers. In terms of facial selectivity, cycloadducts 5a-h and 5'i were obtained as single diastereomers, whereas the reaction of dipole 3j was less selective and gave a mixture of 5j and 5'j in a ratio of 15:85. Stereoselectivity of copper(I) iodide-catalyzed cycloadditions of ethyl propiolate 4 to azomethine imines 3 was controlled by the stereodirecting phenyl group at position 5 and by the ortho-substituents at the 1'-Ar residue.