Reductive Cleavage of N-Substituted 2-Aryl-1,3-oxazolidines: Generation of α-Amino-Substituted Carbanions

Article abstract of DOI:10.1021/jo00076a033

The behavior of several N-substituted 2-aryl-1,3-oxazolidines has been investigated under conditions of electron transfer from alkali metals in aprotic solvents.The reduction led to the regioselective cleavage of the benzylic carbon-oxygen bond, with formation of the corresponding N-substituted benzylamino alcohols in good yields.Investigation of the mechanism of this reductive cleavage, with the aid of labeling experiments, showed the intermediate formation of α-tertiary amino-substituted carbanions.