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Regio- and Stereoselective Electrochemical Alkylation of Morita-Baylis-Hillman Adducts.

ABSTRACT: Electrosynthesis is effectively employed in a general regio- and stereoselective alkylation of Morita-Baylis-Hillman compounds. The exposition of N-acyloxyphthalimides (redox-active esters) to galvanostatic electroreductive conditions, following the sacrificial-anode strategy, is proved an efficient and practical method to access densely functionalized cinnamate and oxindole derivatives. High yields (up to 80%) and wide functional group tolerance characterized the methodology. A tentative mechanistic sketch is proposed based on dedicated control experiments.

SUBMITTER: Bertuzzi G

PROVIDER: S-EPMC9237826 | biostudies-literature | 2022 Jun

REPOSITORIES: biostudies-literature

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Regio- and Stereoselective Electrochemical Alkylation of Morita-Baylis-Hillman Adducts.

Bertuzzi Giulio G Ombrosi Giada G Bandini Marco M

Organic letters 20220614 24

Electrosynthesis is effectively employed in a general regio- and stereoselective alkylation of Morita-Baylis-Hillman compounds. The exposition of <i>N</i>-acyloxyphthalimides (redox-active esters) to galvanostatic electroreductive conditions, following the sacrificial-anode strategy, is proved an efficient and practical method to access densely functionalized cinnamate and oxindole derivatives. High yields (up to 80%) and wide functional group tolerance characterized the methodology. A tentative ...[more]

PMID: 35700274

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