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

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外文摘要：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 toler-ance(＞50 examples).Mechanistic experiments revealed that this reaction involved a Peterson olefination,Michael addition and in-tramolecular C(sp3)arylation cascade.The variegated synthetic derivatization of target products and successful construction of bioac-tive molecules further illustrate the synthetic potential in spirooxindole-related drug discovery.

外文关键词：

Cascade reactionSpirooxindolePeterson olefinationC(sp3)arylation of oxindoleTransition-metal-free

作者：

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

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作者单位：

School of Chemistry and Environmental Engineering,School of Chemical Engineering and Pharmacy,and Key Laboratory of Green Chemical Process,Ministry of Education,Wuhan Institute of Technology,Wuhan,Hubei 430205,China

Key Laboratory of Catalysis and Energy Materials Chemistry of Ministry of Education,School of Chemistry and Materials Science,South-Central University for Nationalities,Wuhan,Hubei 430074,China

出版年：

2024

DOI：

10.1002/cjoc.202400410

中国化学(英文版)

中国化学会上海有机化学研究所

中国化学(英文版)

CSTPCD

影响因子：0.848

ISSN：1001-604X

年,卷(期)：2024.42(21)