A Facile Approach to Tetracyclic Indolines: Highly Diastereoselective [4+2] Annulation of Indoles with Bicyclic N-Substituted Cyclobutanes

Peng Juan Li; Xiao Kang Kuang; Jun Zhu; Yong Tang; Lijia Wang

doi:10.1021/acs.joc.4c02509

A Facile Approach to Tetracyclic Indolines: Highly Diastereoselective [4+2] Annulation of Indoles with Bicyclic N-Substituted Cyclobutanes

Peng Juan Li, Xiao Kang Kuang, Jun Zhu, Yong Tang, Lijia Wang^*

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

Research output: Contribution to journal › Article › peer-review

2 Scopus citations

Abstract

A new stereoselective [4+2] annulation method for constructing tetracyclic indolines by reacting indoles with bicyclic N-substituted cyclobutanes has been developed. Using Sc(OTf)₃ as a catalyst, a series of tetracyclic indolines with four continued stereogenic carbon centers have been obtained in ≤86% yields as single diastereomers. This reaction offers an accessible way for the rapid construction of the core structures of biologically active natural products like paucidirinine, deethylibophyllidine, and ibophyllidine.

Original language	English
Pages (from-to)	899-907
Number of pages	9
Journal	Journal of Organic Chemistry
Volume	90
Issue number	1
DOIs	https://doi.org/10.1021/acs.joc.4c02509
State	Published - 10 Jan 2025

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title = "A Facile Approach to Tetracyclic Indolines: Highly Diastereoselective [4+2] Annulation of Indoles with Bicyclic N-Substituted Cyclobutanes",

abstract = "A new stereoselective [4+2] annulation method for constructing tetracyclic indolines by reacting indoles with bicyclic N-substituted cyclobutanes has been developed. Using Sc(OTf)3 as a catalyst, a series of tetracyclic indolines with four continued stereogenic carbon centers have been obtained in ≤86\% yields as single diastereomers. This reaction offers an accessible way for the rapid construction of the core structures of biologically active natural products like paucidirinine, deethylibophyllidine, and ibophyllidine.",

author = "Li, \{Peng Juan\} and Kuang, \{Xiao Kang\} and Jun Zhu and Yong Tang and Lijia Wang",

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T2 - Highly Diastereoselective [4+2] Annulation of Indoles with Bicyclic N-Substituted Cyclobutanes

AU - Li, Peng Juan

AU - Kuang, Xiao Kang

AU - Zhu, Jun

AU - Tang, Yong

AU - Wang, Lijia

PY - 2025/1/10

Y1 - 2025/1/10

N2 - A new stereoselective [4+2] annulation method for constructing tetracyclic indolines by reacting indoles with bicyclic N-substituted cyclobutanes has been developed. Using Sc(OTf)3 as a catalyst, a series of tetracyclic indolines with four continued stereogenic carbon centers have been obtained in ≤86% yields as single diastereomers. This reaction offers an accessible way for the rapid construction of the core structures of biologically active natural products like paucidirinine, deethylibophyllidine, and ibophyllidine.

AB - A new stereoselective [4+2] annulation method for constructing tetracyclic indolines by reacting indoles with bicyclic N-substituted cyclobutanes has been developed. Using Sc(OTf)3 as a catalyst, a series of tetracyclic indolines with four continued stereogenic carbon centers have been obtained in ≤86% yields as single diastereomers. This reaction offers an accessible way for the rapid construction of the core structures of biologically active natural products like paucidirinine, deethylibophyllidine, and ibophyllidine.

UR - https://www.scopus.com/pages/publications/85214664378

U2 - 10.1021/acs.joc.4c02509

DO - 10.1021/acs.joc.4c02509

M3 - 文章

AN - SCOPUS:85214664378

SN - 0022-3263

VL - 90

SP - 899

EP - 907

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 1

ER -

A Facile Approach to Tetracyclic Indolines: Highly Diastereoselective [4+2] Annulation of Indoles with Bicyclic N-Substituted Cyclobutanes

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