Copper-Catalyzed Enantioselective [2+2] Cycloadditions of 2-Nitrosopyridine with Ketenes
Copper-Catalyzed Enantioselective [2+2] Cycloadditions of 2-Nitrosopyridine with Ketenes
复制标题
DOI：
10.1002/adsc.201000153
复制
发表时间：
2010-04
影响因子：
5.4
通讯作者：
I. Chatterjee;C. Jana;M. Steinmetz;S. Grimme;A. Studer
中科院分区：
文献类型：
--
作者：
I. Chatterjee;C. Jana;M. Steinmetz;S. Grimme;A. Studer
铜(I)催化的各种乙烯酮与2-亚硝基吡啶的[2 + 2]环加成反应可产生具有高合成价值的1,2-氧杂氮杂环丁烷-3-酮，并且具有良好的对映选择性。热非催化过程提供了不稳定的区域异构体氧氮杂环丁酮。密度函数理论 (DFT) 计算证明该反应通过协调的 [2+2] 环加成途径发生。
Copper(I)-catalyzed [2 + 2] cycloadditions of various ketenes with 2-nitrosopyridine to afford synthetically highly valuable 1,2-oxazetidine-3-ones are shown to occur with good enantioselectivities. The thermal uncatalyzed process furnishes the unstable regioisomeric oxazetidinone. Density function theory (DFT) calculations give evidence that the reaction occurs via a concerted [2+2] cycloaddtion pathway.