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Updated: Sep 16, 2025
Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Rh-Catalyzed Atroposelective Single-Carbon Insertion
Bowen Li1, Valero G Alfonso1,2, Alessio Puggioli1,2
1Institute of Chemical Research of Catalonia (ICIQ-CERCA), The Barcelona Institute of Science and Technology, Països Catalans 16, 43007 Tarragona, Spain.
Abstract:
Single-carbon insertion processes have gained considerable momentum over the past few years. Although innovative methods have emerged for converting indole or indene into quinoline or naphthalene cores, the enantioselective version of such ring-expansions to create (hetero)biaryl atropisomers has not been developed. Herein, we report the first enantioselective single-carbon insertion that converts 3-aryl indoles to atropochiral quinolines. Key in the process was the generation of a chiral Rh-carbynoid that mediated in the creation of the stereogenic C(sp2)-C(sp2) axis.
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