Chinese Journal of Organic Chemistry >
Cascade Cyclization Reaction Initiated by Benzylic Carbocation of Indole: Scope and Mechanistic Insights
Received date: 2021-02-01
Revised date: 2021-05-02
Online published: 2021-05-25
Supported by
National Natural Science Foundation of China(21871013)
During the course of the total synthesis of α-cyclopianic acid (α-CPA) and speradine C, our research group have developed a biomimetic cascade cyclization reaction initiated by the benzylic carbocation of indole. In this paper, the scope and the reaction mechanism of the cascade cyclization reaction were studied. The experimental results show that the cascade cyclization reaction occurrs at the benzylic carbocation of indole, indicating that the conjugation effect of the indole nitrogen atom plays a key role in the cascade cyclization of benzylic carbocations.
Key words: mechanism; cascade cyclization; benzylic carbocation; indole; conjugation effect
Zhongrun Gao , Yuan Wang , Hang Song , Zhengren Xu , Yanxing Jia . Cascade Cyclization Reaction Initiated by Benzylic Carbocation of Indole: Scope and Mechanistic Insights[J]. Chinese Journal of Organic Chemistry, 2021 , 41(8) : 3126 -3133 . DOI: 10.6023/cjoc202102006
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