Spirooxindole is an important scaffold found frequently in natural products and biologically active molecules. Easy construction of spirooxindole derivatives with simple starting material is significant for natural product synthesis, drug discovery and biomedical research. Compared with the intensively studied C3 spirooxindoles, the development of reliable approaches for the formation of a structurally analogous spiropseudoindoxyl scaffold containing a spirocyclic quaternary carbon center at the C2 position is finite. We have learned that sulfur ylides as excellent synthons are widely used for the construction of aziridines or cyclopropanes with imines or electron-deficient olefins. We hypothesize that sulfur ylides can readily react with easily available (Z)-2-ylideneoxindoles to assemble a spirocyclopropane moiety at the C2-position of indole through 1,4-addition/substitution cyclization. Here, we report our development of a mild and efficient method for diastereoselective synthesis of cyclopropanefused C2-spiropseudoindoxyl derivatives.

Efficient synthesis of cyclopropane-fused spiro-pseudoindoxyl derivatives through highly diastereoselective [2 + 1] annulation

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.