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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Electrochemical control of regioselective ring opening enables divergent functionalization of methylenecyclopropanes
Hongqiang Liu1, Xinyu Chen2, Qianlong Zhang2
1Anhui Intermedia Technology Co., Ltd., Bengbu, Anhui 233000, P. R. China. hongjili@chnu.edu.cn.
Abstract:
Herein, we report an electrochemically controlled regioselective ring-opening of methylenecyclopropanes (MCPs), providing a range of substituted indole derivatives and chloro-substituted alkenes in moderate to good yields. The tunable transformations proceed under mild and oxidant-free conditions through electrochemically generated N-centered radicals. Mechanistic studies reveal that water molecules serve as the oxygen source, facilitating subsequent installation of a tosylate (OTs) group that offers versatile opportunities for late-stage derivatization.
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