Michael Addition/Hemiketalization Cascade Reaction Between β-Dicarbonyl Compounds and Isatin-Derived α,β-Unsaturated Ketones to Construct 3,4'-Pyran-spirooxindoles

doi:10.6023/cjoc202406026

Abstract

3,4'-Pyran-spirooxindole is a structural unit existing in many natural products and bioactive synthetic compounds. The synthesis of multifunctionalized 3,4'-pyran-spirooxindole derivatives has rarely been reported. Herein a Michael addition/hemiketalization cascade reaction between β-dicarbonyl compounds and isatin-derived α,β-unsaturated ketones catalyzed by 4-dimethylaminopyridine (DMAP) is presented. A variety of multifunctionalized 3,4'-pyran-spirooxindoles were obtained in high yields (up to 99%) with excellent diastereoselectivities (dr>20∶1) under mild conditions. This methodology provides a simple and convenient method for the syntheses of multifunctionalized 3,4'-pyran-spirooxindoles.

Key words: cascade reaction, catalysis, Michael addition, pyran, spirooxindole

Cite this article

Mingmei Zhang, Feng Sha, Xin-Yan Wu. Michael Addition/Hemiketalization Cascade Reaction Between β-Dicarbonyl Compounds and Isatin-Derived α,β-Unsaturated Ketones to Construct 3,4'-Pyran-spirooxindoles[J]. Chinese Journal of Organic Chemistry, 2025, 45(4): 1369-1378.

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β-二羰基化合物与靛红衍生的α,β-不饱和酮之间的Michael加成/半缩酮化串联反应构建3,4'-吡喃-螺环氧化吲哚类化合物