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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 |

REPOSITORIES: biostudies-literature

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Asymmetric allylic alkylation of Morita-Baylis-Hillman carbonates with ?-fluoro-?-keto esters.

Project description:In the presence of a commercially available Cinchona alkaloid as catalyst, the asymmetric allylic alkylation of Morita-Baylis-Hillman carbonates, with ?-fluoro-?-keto esters as nucleophiles, have been successfully developed. A series of important fluorinated adducts, with chiral quaternary carbon centres containing a fluorine atom, was achieved in good yields (up to 93%), with good to excellent enantioselectivities (up to 96% ee) and moderate diastereoselectivities (up to 4:1 dr).

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Morita-Baylis-Hillman Adducts Display Anti-Inflammatory Effects by Modulating Inflammatory Mediator Expression in RAW264.7 Cells.

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Organocatalytic asymmetric allylic amination of Morita-Baylis-Hillman carbonates of isatins.

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