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.

Giulio Bertuzzi, G.O. (2022). Regio- and Stereoselective Electrochemical Alkylation of Morita−Baylis−Hillman Adducts. ORGANIC LETTERS, 24, 4354-4359 [10.1021/acs.orglett.2c01529].

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

Giulio Bertuzzi
Conceptualization
;
Marco Bandini
Conceptualization
2022

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.
2022
Giulio Bertuzzi, G.O. (2022). Regio- and Stereoselective Electrochemical Alkylation of Morita−Baylis−Hillman Adducts. ORGANIC LETTERS, 24, 4354-4359 [10.1021/acs.orglett.2c01529].
Giulio Bertuzzi, Giada Ombrosi, Marco Bandini
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/891406
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