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Updated: Feb 21, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Iridium-Catalyzed Asymmetric Allylic Dearomatization by a Desymmetrization Strategy
Ye Wang1, Chao Zheng1, Shu-Li You1,2
1State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, China.
Abstract:
A desymmetrization strategy was developed involving iridium-catalyzed allylic dearomatization of indoles. The six-membered-ring spiroindolenines contain three contiguous stereogenic centers, including an all-carbon quaternary center, and were obtained in up to 99 % yield with 99 % ee and >95:5 d.r. When treated with a catalytic amount of tosylic acid, six-membered spiroindolenine undergoes an unprecedented six-to-seven-membered ring expansion, affording the corresponding hexahydroazepino[4,5-b]indole.
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