Bridged-Type Selective Intramolecular Nitrone–Alkene Cycloaddition: Computational Chemistry-Inspired Regioselectivity Control

A regioselective intramolecular nitrone-alkene cycloaddition for synthesizing oxazabicyclo ring-fused indoles is reported. Computational studies guided the development of optimal conditions using In(OTf)<sub>3</sub> as a Lewis acidic reagent. This method demonstrates a broad substrate scope, forming seven- and eight-membered carbocycles with various substituents, and provides a versatile route to complex nitrogen-containing scaffolds with potential applications in medicinal chemistry and the total synthesis of biologically active compounds.

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Publication Details

Journal
Organic Letters
Published
2025-02-05
DOI
https://doi.org/10.1021/acs.orglett.5c00125
Citations
6
Primary Topic
Asymmetric Synthesis and Catalysis
Type
article
Field-Weighted Citation Impact
5.62

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article

Bridged-Type Selective Intramolecular Nitrone–Alkene Cycloaddition: Computational Chemistry-Inspired Regioselectivity Control

Tetsuhiro Nemoto, Tomohiro Yazawa, Tanawat Phumjan, Shinji Harada
6 citations
Organic Letters
Asymmetric Synthesis and Catalysis
5.62
article

Bridged-Type Selective Intramolecular Nitrone–Alkene Cycloaddition: Computational Chemistry-Inspired Regioselectivity Control

Tetsuhiro Nemoto, Tomohiro Yazawa, Tanawat Phumjan, Shinji Harada
article en
6 citations

Abstract

A regioselective intramolecular nitrone-alkene cycloaddition for synthesizing oxazabicyclo ring-fused indoles is reported. Computational studies guided the development of optimal conditions using In(OTf)<sub>3</sub> as a Lewis acidic reagent. This method demonstrates a broad substrate scope, forming seven- and eight-membered carbocycles with various substituents, and provides a versatile route to complex nitrogen-containing scaffolds with potential applications in medicinal chemistry and the total synthesis of biologically active compounds.

Organic LettersVol. 27(6)
Chiba University (JP)
Fugaku Trust for Medicinal Research, Japan Society for the Promotion of Science, Institute for Global Prominent Research, Chiba University
Openalex Percentile: Top 5%
Asymmetric Synthesis and Catalysis
5.62
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Bridged-Type Selective Intramolecular Nitrone–Alkene Cycloaddition: Computational Chemistry-Inspired Regioselectivity Control — Tetsuhiro Nemoto, Tomohiro Yazawa, et al. · Organic Letters (2025) | TGRS Research Map | TGRS