Stereoselective Electrosynthesis of Imidazolines through Coupling and Ring Restructuring of Alkoxyoxazoles with α-Amino Carbonyls

The established strategy unveils metal- and exogenous oxidant-free electrochemical heterocoupling and ring restructuring of alkoxyoxazoles with α-amino carbonyls, furnishing diversely substituted <i>trans</i>-imidazoline scaffolds. This controlled electro-redox coupling and subsequent Brønsted acid-mediated epimerization successfully prevent undesired oxidative aromatization and precisely provide two contiguous stereocenters as a part of the five-membered heterocycle. An extensive range of distinct functionalities is well-tolerated, resulting in a broad substrate scope. Detailed mechanistic investigations enhance the comprehension of the reaction mechanism.