通过[2 + 2]环加成反应立体选择性构建高官能化氮杂环丁烷。
Stereoselective construction of highly functionalized azetidines via a [2 + 2]-cycloaddition.
机构信息
Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433, China, and Shanghai Key Laboratory of Molecular Catalysts and Innovative Materials, Department of Chemistry, Fudan University, Shanghai 200433, China.
出版信息
Org Lett. 2010 Jun 18;12(12):2802-5. doi: 10.1021/ol100885f.
A facile stereoselective synthesis of highly functionalized azetidines from a novel [2 + 2]-cycloaddition of 2-aminomalonates to chalcones is reported. The desired four-membered ring construction proceeded via a grind-promoted solvent-free Michael addition and a PhIO/Bu(4)NI mediated oxidative cyclization and afforded azetidines in moderate to good yields with excellent diastereoselectivities.
本文报道了一种新型[2+2]环加成反应，即 2-氨甲基丙二酸酯与查尔酮的立体选择性反应，可从简单原料高立体选择性合成高度官能化的氮杂环丁烷。该四元环的构建过程涉及研磨促进的无溶剂迈克尔加成和 PhIO/Bu(4)NI 介导的氧化环化反应，以中等至良好的收率和优异的非对映选择性得到氮杂环丁烷。
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