Zinc-Mediated C‑3 α‑Prenylation of Isatins with Prenyl Bromide: Access to 3‑Prenyl-3-hydroxy-2-oxindoles and Its Application

Zinc-Mediated C‑3 α‑Prenylation of Isatins with Prenyl Bromide: Access to 3‑Prenyl-3-hydroxy-2-oxindoles and Its Application

A convenient and highly α-regioselective strategy for the synthesis of 3-prenyl-3-hydroxy-2-oxindoles has been developed starting from isatins and prenylzinc with good to excellent yields. This protocol provides a straightforward and practical way to introduce an α-prenyl moiety into the C-3 positio...

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Veröffentlicht in:Journal of organic chemistry 2016-07, Vol.81 (13), p.5487-5494
Hauptverfasser: Zhao, Li-Ming, Zhang, Ai-Li, Zhang, Jie-Huan, Gao, Hua-Shuai, Zhou, Wei
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container_issue 13
container_start_page 5487
container_title Journal of organic chemistry
container_volume 81
creator Zhao, Li-Ming
Zhang, Ai-Li
Zhang, Jie-Huan
Gao, Hua-Shuai
Zhou, Wei
description A convenient and highly α-regioselective strategy for the synthesis of 3-prenyl-3-hydroxy-2-oxindoles has been developed starting from isatins and prenylzinc with good to excellent yields. This protocol provides a straightforward and practical way to introduce an α-prenyl moiety into the C-3 position of isatins. The advantages of this reaction are use of the cheap and readily available reagents, operational simplicity, and wide substrate scope. Furthermore, this transformation was applied to the synthesis of several oxindole-containing natural products, which further demonstrated the synthetic utility of this methodology.
doi_str_mv 10.1021/acs.joc.6b00836
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title Zinc-Mediated C‑3 α‑Prenylation of Isatins with Prenyl Bromide: Access to 3‑Prenyl-3-hydroxy-2-oxindoles and Its Application
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