Intermolecular Formal Cycloaddition of Indoles with Bicyclobutanes by Lewis Acid Catalysis

Herein, we develop a new approach to directly access architecturally complex polycyclic indolines from readily available indoles and bicyclo[1.1.0]butanes (BCBs) through formal cycloaddition promoted by commercially available Lewis acids. The reaction proceeded through a stepwise pathway involving a...

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Veröffentlicht in:	Angewandte Chemie International Edition 2023-11, Vol.62 (48)
Hauptverfasser:	Ni, Dongshun, Hu, Sai, Tan, Xiangyu, Yang, Yu, Li, Zhenghua, Deng, Li
Format:	Artikel
Sprache:	eng
Schlagworte:	Butanes Catalysis Cycloaddition Heterocyclic compounds Indoles Lewis acid
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creator	Ni, Dongshun Hu, Sai Tan, Xiangyu Yang, Yu Li, Zhenghua Deng, Li
description	Herein, we develop a new approach to directly access architecturally complex polycyclic indolines from readily available indoles and bicyclo[1.1.0]butanes (BCBs) through formal cycloaddition promoted by commercially available Lewis acids. The reaction proceeded through a stepwise pathway involving a nucleophilic addition of indoles to BCBs followed by an intramolecular Mannich reaction to form rigid indoline‐fused polycyclic structures, which resemble polycyclic indole alkaloids. This new reaction tolerated a wide range of indoles and BCBs, thereby allowing the one‐step construction of various rigid indoline polycycles containing up to four contiguous quaternary carbon centers.
doi_str_mv	10.1002/anie.202308606
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subjects	Butanes Catalysis Cycloaddition Heterocyclic compounds Indoles Lewis acid
title	Intermolecular Formal Cycloaddition of Indoles with Bicyclobutanes by Lewis Acid Catalysis
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