Modular Assembly of Six-Membered Carbocyclic Spirooxindoles via Peterson Olefination/Michael Addition/C(sp3) Arylation Cascade

Feng-Cheng Jia; Zi-Yi Yuan; Na Luo; Shuang-Xi Gu; Xiao-Qiang Hu

doi:10.1002/cjoc.202400410

Chinese Journal of Chemistry ›› 2024, Vol. 42 ›› Issue (21) : 2614 -2620. DOI: 10.1002/cjoc.202400410

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Modular Assembly of Six-Membered Carbocyclic Spirooxindoles via Peterson Olefination/Michael Addition/C(sp3) Arylation Cascade

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Abstract

Concise assembly of spirooxindoles is of great significance but a challenging task in modern organic synthesis. Described herein is an unusual base-promoted [4+2] spiroannulation of rarely used isatin-derived β-silylcarbinols with o-halogen aromatic ketones, which enables rapid and modular synthesis of six-membered carbocyclic spirooxindoles in high yields with excellent functional group tolerance (> 50 examples). Mechanistic experiments revealed that this reaction involved a Peterson olefination, Michael addition and intramolecular C(sp ³) arylation cascade. The variegated synthetic derivatization of target products and successful construction of bioactive molecules further illustrate the synthetic potential in spirooxindole-related drug discovery.

Keywords

Cascade reaction / Spirooxindole / Peterson olefination / C(sp ³) arylation of oxindole / Transition-metal-free

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Feng-Cheng Jia, Zi-Yi Yuan, Na Luo, Shuang-Xi Gu, Xiao-Qiang Hu. Modular Assembly of Six-Membered Carbocyclic Spirooxindoles via Peterson Olefination/Michael Addition/C(sp3) Arylation Cascade. Chinese Journal of Chemistry, 2024, 42(21): 2614-2620 DOI:10.1002/cjoc.202400410