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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
- Zhang, Xia, Wang, Xiaoyan, He, Yanyang, Liu, Ying, Liu, Jie, Shi, Jianyou
- Tetrahedron letters 2016 v.57 pp. 1143-1145
- X-ray diffraction, aldehydes, chemical structure, cycloaddition reactions, nuclear magnetic resonance spectroscopy, stereochemistry
- 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.