Efficient construction of highly functionalized pyrrolo[1,2-c]imidazol-1-ones via a regioselective 1,3-dipolar cycloaddition of imidazolidin-4-ones, aldehydes, and nitroalkenes in one pot

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• 作者：Xia Zhang^a ; ^&dagger ; ; Xiaoyan Wang^b ; ^&dagger ; ; Yanyang He^a ; ^c ; Ying Liu^a ; Jie Liu^a ; ^{liujie2011@scu.edu.cn" class="auth_mail" title="E-mail the corresponding author} ; Jianyou Shi^a ; ^c ; ^{shijianyoude@126.com" class="auth_mail" title="E-mail the corresponding author}
• 关键词：1 ; 3-Dipolar cycloaddition ; Pyrrolo[1 ; 2-c]imidazol-1-one ; Imidazolidin-4-one ; Nitroalkene ; Regioselective
• 刊名：Tetrahedron Letters
• 出版年：2016
• 出版时间：9 March 2016
• 年：2016
• 卷：57
• 期：10
• 页码：1143-1145
• 全文大小：617 K

文摘

A series of novel pyrrolo[1,2-c]imidazol-1-ones were efficiently synthesized via a three-component, regioselective 1,3-dipolar cycloaddition reaction. The azomethine ylides generated in situ from imidazolidin-4-ones and aldehydes reacted with the nitroalkenes to yield the novel pyrrolo[1,2-c]imidazol-1-one derivatives with multiple stereogenic centers in moderate to high yields (up to 99%) and in high diastereoselectivities (up to 98:2). The structure and relative stereochemistry of cycloadducts were confirmed by ¹H NMR spectroscopy and X-ray crystallography.