Protecting group-directed annulations of tetra-substituted oxindole olefins and sulfur ylides: Regio- and chemoselective synthesis of cyclopropane- and dihydrofuran-fused spirooxindoles

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Abstract

Protecting group-controlled annulations of tetra-substituted oxindole olefins and sulfur ylides have been achieved for the synthesis of multifunctional cyclopropane- and dihydrofuran-fused spirooxindoles. Under precise annulation regulation, a variety of cyclopropane- and dihydrofuran-fused spirooxindoles containing vicinal quaternary carbon centers were produced in up to 90% yield with up to 20:1 dr. This reaction demonstrates high regio-, chemo- and diastereoselectivity, broad functional group tolerance and gram-scale capacity.

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Kang, J. W., Li, X., Chen, F. Y., Luo, Y., Zhang, S. C., Kang, B., … Han, B. (2019). Protecting group-directed annulations of tetra-substituted oxindole olefins and sulfur ylides: Regio- and chemoselective synthesis of cyclopropane- and dihydrofuran-fused spirooxindoles. RSC Advances, 9(22), 12255–12264. https://doi.org/10.1039/c9ra02192b

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