Electroreductive Divergent Hydrolysis and Hydrogenation of 2-Oxazolidinones

Abstract

The ring-opening transformation of 2-oxazolidinones remains a highly efficacious approach for constructing high-value N-containing precision chemicals. Herein, we report a highly efficient electroreductive approach for the selective hydrogenation and hydrolysis of 2-oxazolidinones. The addition of H2O plays a crucial role in modulating the chemoselectivity of the electroreduction, enabling access to various chiral amino alcohols and amines. This method is amenable to gram-scale synthesis, and the resulting chiral amino alcohols serve as valuable synthetic precursors to diverse chiral N-containing compounds. Detailed mechanistic studies provided support for an unprecedented single electron transfer (SET) pathway for the hydrogenation and base-promoted hydrolysis.