☆ 4.7 Article

Construction of Spirocyclopropane-Linked Heterocycles Containing Both Pyrazolones and Oxindoles through Michael/Alkylation Cascade Reactions

JOURNAL OF ORGANIC CHEMISTRY (2015)

期刊

JOURNAL OF ORGANIC CHEMISTRY

卷 80, 期 22, 页码 11369-11377

出版社

AMER CHEMICAL SOC

DOI: 10.1021/acs.joc.5b01940

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Chemistry, Organic

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National Natural Science Foundation of China [21272024]

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An effective diastereoselective Michael/alkylation cascade reaction of arylidenepyrazolones with 3-chlorooxindoles catalyzed by DIPEA was developed. A variety of highly functionalized spiro-pyrazolone-cyclopropane-oxindoles were obtained in excellent yields (up to 99%) with good to excellent diastereoselectivities (up to >25:1 dr). Moreover, the squaramide-catalyzed asymmetric reactions of arylidenepyrazolones with 3-chlorooxindoles afforded the corresponding chiral spirocyclic heterocycles in excellent yields (up to 99%) with moderate diastereoselectivities (up to 87:13 dr) and moderate to high enantioselectivities (up to 74% ee).

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