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Updated: Sep 16, 2025

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Published on: May 26, 2019

Rh-Catalyzed Atroposelective Single-Carbon Insertion.

Bowen Li¹, Valero G Alfonso^1,2, Alessio Puggioli^1,2

¹Institute of Chemical Research of Catalonia (ICIQ-CERCA), The Barcelona Institute of Science and Technology, Països Catalans 16, 43007 Tarragona, Spain.

Journal of the American Chemical Society

|July 7, 2025

Summary

Researchers developed the first enantioselective single-carbon insertion method. This novel process converts 3-aryl indoles into valuable atropochiral quinolines, advancing asymmetric synthesis.

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Area of Science:

Organic Chemistry
Asymmetric Synthesis
Catalysis

Background:

Single-carbon insertion reactions are increasingly important in organic synthesis.
Existing methods for indole/indene conversion lack enantioselectivity for creating chiral atropisomers.

Purpose of the Study:

To develop the first enantioselective single-carbon insertion for synthesizing atropochiral quinolines.
To establish a method for creating stereogenic C(sp2)-C(sp2) axes in (hetero)biaryl systems.

Main Methods:

Utilized a chiral Rh-carbynoid intermediate.
Developed a novel ring-expansion reaction of 3-aryl indoles.

Main Results:

Successfully achieved enantioselective single-carbon insertion.
Synthesized atropochiral quinolines from 3-aryl indoles with high stereocontrol.
Demonstrated the generation of a stereogenic C(sp2)-C(sp2) axis.

Conclusions:

This study reports the first enantioselective single-carbon insertion for synthesizing atropochiral quinolines.
The developed method offers a new route to valuable chiral molecules.
Highlights the utility of chiral Rh-carbynoids in asymmetric catalysis.