Modular Assembly of Six-Membered Carbocyclic Spirooxindoles via Peterson Olefination/Michael Addition/C(sp^(3))Arylation Cascade  

作　　者：Feng-Cheng Jia Zi-Yi Yuan Na Luo Shuang-Xi Gu Xiao-Qiang Hu 

机构地区：[1]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 [2]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　　处：《Chinese Journal of Chemistry》2024年第21期2614-2620,共7页中国化学（英文版）

基　　金：financial support of National Natural Science Foundation of China(21901193,22271314 and 22377097);the innovation foundation of Key Laboratory of Green Chemical Engineering Process of Ministry of Education(GCX2023002).

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-derivedβ-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.

关 键 词：Cascade reaction SPIROOXINDOLE Peterson olefination C(sp^(3))arylation of oxindole Transition-metal-free 

分 类 号：O62[理学—有机化学]