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

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.

Automated summary

This study demonstrates the effective and practical use of electrosynthesis for regio- and stereoselective alkylation of Morita-Baylis-Hillman compounds, resulting in high yields and wide functional group tolerance. It provides an efficient method for accessing densely functionalized cinnamate and oxindole derivatives.