Generation of Functionalized Azepinone Derivatives via a (4 + 3)-Cycloaddition of Vinyl Ketenes and α‑Imino Carbenes Derived from N‑Sulfonyl-triazoles

Generation of Functionalized Azepinone Derivatives via a (4 + 3)-Cycloaddition of Vinyl Ketenes and α‑Imino Carbenes Derived from N‑Sulfonyl-triazoles

An intermolecular RhII-catalyzed, formal (4 + 3)-cycloaddition between vinyl ketenes and N-sulfonyl-1,2,3-triazoles for the construction of azepinone products is described. Employing vinyl ketenes as a 1,4-dipolar surrogate, instead of the more commonly used dienyl moieties, allows for the intermole...

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Veröffentlicht in:Journal of organic chemistry 2022-03, Vol.87 (5), p.3825-3833
Hauptverfasser: Hill, Harrison M, Tucker, Zachary D, Rodriguez, Kevin X, Wendt, Katelyn A, Ashfeld, Brandon L
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Sprache:eng
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Catalysis
Cycloaddition Reaction
Rhodium
Triazoles
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container_end_page 3833
container_issue 5
container_start_page 3825
container_title Journal of organic chemistry
container_volume 87
creator Hill, Harrison M
Tucker, Zachary D
Rodriguez, Kevin X
Wendt, Katelyn A
Ashfeld, Brandon L
description An intermolecular RhII-catalyzed, formal (4 + 3)-cycloaddition between vinyl ketenes and N-sulfonyl-1,2,3-triazoles for the construction of azepinone products is described. Employing vinyl ketenes as a 1,4-dipolar surrogate, instead of the more commonly used dienyl moieties, allows for the intermolecular and selective formation of azepinone products over a potential (3 + 2)-cycloadduct under mild reaction conditions allows for the generation of azepinone products in up to 98% yield.
doi_str_mv 10.1021/acs.joc.1c03002
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subjects Catalysis
Cycloaddition Reaction
Rhodium
Triazoles
title Generation of Functionalized Azepinone Derivatives via a (4 + 3)-Cycloaddition of Vinyl Ketenes and α‑Imino Carbenes Derived from N‑Sulfonyl-triazoles
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