Copper-Catalyzed Disruption of a Cascade Reaction: Synthesis of γ-Ketoamides from Nitrones and Ynamides DOI Creative Commons

Abdullah S. Alshreimi,

Esther Shim,

Donald J. Wink

et al.

Published: April 30, 2024

A thermal dipolar cycloaddition and rearrangement reaction to form pyrrolines has been redirected towards the synthesis of γ-ketoamides from nitrones ynamides with a Cu(II) catalyst. An iminium N,O-dialkenylhydroxylamine intermediate is proposed initiate diastereoselective C–C bond formation combination copper catalyst nitrone protecting group balance desired reactivity, diastereoselectivity, sensitivity hydrolysis. Reaction optimization described in addition scope, mechanistic studies, conversion 1,4-diones. This catalytic method controls central 1,4-dicarbonyl compounds showcases unique reactivity N-alkenylnitrones for accessing these molecules.

Language: Английский

Copper-Catalyzed Disruption of a Cascade Reaction: Synthesis of γ-Ketoamides from Nitrones and Ynamides DOI Creative Commons

Abdullah S. Alshreimi,

Esther Shim,

Donald J. Wink

et al.

Published: April 30, 2024

A thermal dipolar cycloaddition and rearrangement reaction to form pyrrolines has been redirected towards the synthesis of γ-ketoamides from nitrones ynamides with a Cu(II) catalyst. An iminium N,O-dialkenylhydroxylamine intermediate is proposed initiate diastereoselective C–C bond formation combination copper catalyst nitrone protecting group balance desired reactivity, diastereoselectivity, sensitivity hydrolysis. Reaction optimization described in addition scope, mechanistic studies, conversion 1,4-diones. This catalytic method controls central 1,4-dicarbonyl compounds showcases unique reactivity N-alkenylnitrones for accessing these molecules.

Language: Английский

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