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

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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… Click to show full 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.

Keywords: morita baylis; regio stereoselective; baylis hillman; alkylation morita

Journal Title: Organic Letters
Year Published: 2022

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