Bridged-Type Selective Intramolecular Nitrone–AlkeneCycloaddition: 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.

Publication Details

Journal
Figshare
Published
2025-02-05
DOI
https://doi.org/10.1021/acs.orglett.5c00125.s001
Primary Topic
Prenatal Screening and Diagnostics
Type
article
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article

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

Figshare
Prenatal Screening and Diagnostics
article

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

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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.

Figshare
Clean water and sanitation
Openalex Percentile: Top 41%
Prenatal Screening and Diagnostics
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Bridged-Type Selective Intramolecular Nitrone–AlkeneCycloaddition: Computational Chemistry-Inspired Regioselectivity Control · Figshare (2025) | TGRS Research Map | TGRS