Photoredox-catalyzed diastereoselective dearomative prenylation and reverse-prenylation of electron-deficient indole derivatives

Xuexue Chang, Fangqing Zhang, Shibo Zhu, Zhuang Yang, Xiaoming Feng () and Yangbin Liu ()
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Xuexue Chang: Shenzhen Bay Laboratory
Fangqing Zhang: Shenzhen Bay Laboratory
Shibo Zhu: Shenzhen Bay Laboratory
Zhuang Yang: West China Hospital of Sichuan University
Xiaoming Feng: Shenzhen Bay Laboratory
Yangbin Liu: Shenzhen Bay Laboratory

Nature Communications, 2023, vol. 14, issue 1, 1-12

Abstract: Abstract Prenylated and reverse-prenylated indolines are privileged scaffolds in numerous naturally occurring indole alkaloids with a broad spectrum of important biological properties. Development of straightforward and stereoselective methods to enable the synthesis of structurally diverse prenylated and reverse-prenylated indoline derivatives is highly desirable and challenging. In this context, the most direct approaches to achieve this goal generally rely on transition-metal-catalyzed dearomative allylic alkylation of electron-rich indoles. However, the electron-deficient indoles are much less explored, probably due to their diminished nucleophilicity. Herein, a photoredox-catalyzed tandem Giese radical addition/Ireland–Claisen rearrangement is disclosed. Diastereoselective dearomative prenylation and reverse-prenylation of electron-deficient indoles proceed smoothly under mild conditions. An array of tertiary α-silylamines as radical precursors is readily incorporated in 2,3-disubstituted indolines with high functional compatibility and excellent diastereoselectivity (>20:1 d.r.). The corresponding transformations of the secondary α-silylamines provide the biologically important lactam-fused indolines in one-pot synthesis. Subsequently, a plausible photoredox pathway is proposed based on control experiments. The preliminary bioactivity study reveals a potential anticancer property of these structurally appealing indolines.

Date: 2023
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DOI: 10.1038/s41467-023-39633-9

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