A de novo Synthesis of Oxindoles from Cyclohexanone-Derived γ-Keto-Ester Acceptors Using a Desaturative Amination–Cyclization Approach

Henry P. Caldora; Sebastian Govaerts; Shashikant U. Dighe; Oliver J. Turner; Daniele Leonori

doi:10.1055/a-1538-8429

Synthesis, Table of Contents

Synthesis 2021; 53(22): 4272-4278
DOI: 10.1055/a-1538-8429

special topic

Special Issue dedicated to Prof. Sarah Reisman, recipient of the 2019 Dr. Margaret Faul Women in Chemistry Award

A de novo Synthesis of Oxindoles from Cyclohexanone-Derived γ-Keto-Ester Acceptors Using a Desaturative Amination–Cyclization Approach

Henry P. Caldora‡

^aDepartment of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, UK

,

Sebastian Govaerts‡

^aDepartment of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, UK

,

Shashikant U. Dighe

^aDepartment of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, UK

,

Oliver J. Turner

^bOncology R&D, Research & Early Development, AstraZeneca, Darwin building, 310, Cambridge Science Park, Milton Road, Cambridge CB4 0WG, UK

,

Daniele Leonori ∗

^aDepartment of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, UK

› Author Affiliations

Abstract

All articles of this category

Dedicated to Prof Sarah Reisman in recognition on her award of the inaugural Margaret Faul Women in Chemistry Award.

Abstract

Here we report a desaturative approach for oxindole synthesis. This method uses simple ethyl 2-(2-oxocyclohexyl)acetates and primary amine building blocks as coupling partners. A dual photoredox–cobalt manifold is used to generate a secondary aniline that, upon heating, cyclizes with the pendent ester functionality. The process operates under mild conditions and was applied to the modification of several amino acids, the blockbuster drug mexiletine, as well as the formation of dihydroquinolinones.

Key words

photoredox - cobalt catalysis - dehydrogenative amination - late-stage modification - amino acids - oxindole

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References

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