通过氮杂曼尼希引发的氨基磺酸酯衍生的环状亚胺与α-卤代异羟肟酸的环化反应实现对4-咪唑啉酮的区域和非对映选择性合成。
Regio- and Diastereoselective Access to 4-Imidazolidinones via an Aza-Mannich Initiated Cyclization of Sulfamate-Derived Cyclic Imines with α-Halo Hydroxamates.
作者信息
Zhou Jing, Zhang Hong, Chen Xue-Lian, Qu Ya-Li, Zhu Qianqian, Feng Chen-Guo, Chen Ya-Jing
机构信息
School of Pharmaceutical Sciences; Key Laboratory of Advanced Drug Preparation Technologies, Ministry of Education of China; Co-innovation Center of Henan Province for New Drug R&D and Preclinical Safety , Zhengzhou University , 100 Science Avenue , Zhengzhou , Henan 450001 , PR China.
Mineral Processing and Biometallurgy Institute , Rock and Mineral Testing Center of Henan Province , 28 Jinshui Road , Zhengzhou , Henan 450012 , PR China.
出版信息
J Org Chem. 2019 Jul 19;84(14):9179-9187. doi: 10.1021/acs.joc.9b01128. Epub 2019 Jun 27.
An efficient regio- and diastereoselective cyclization of sulfamate-derived cyclic imines with unsubstituted or monosubstituted α-halo hydroxamates is developed under mild conditions. This reaction proceeds smoothly under transition-metal-free conditions via a domino aza-Mannich addition/intramolecular nucleophilic substitution sequence, providing a convenient route to access 2-monosubstituted and 2,5-disubstituted 4-imidazolidinones. Notably, the products were obtained with single -isomers in moderate to excellent yields.
在温和条件下，实现了由氨基磺酸酯衍生的环状亚胺与未取代或单取代的α-卤代异羟肟酸酯进行高效的区域和非对映选择性环化反应。该反应在无过渡金属条件下通过多米诺氮杂-Mannich加成/分子内亲核取代序列顺利进行，为制备2-单取代和2,5-二取代的4-咪唑烷酮提供了一条便捷途径。值得注意的是，产物以单一异构体形式得到，产率中等至优异。
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