Über die Stereochemie der Hydrogenolyse von N‐Benzyl‐Bindungen I. Die Hydrogenolyse von Derivaten der 2‐Amino‐2‐phenyl‐propionsäure.

The stereochemistry of the hydrogenolysis of benzyl‐N bonds was studied using S (+)‐2‐dimethylamino‐2‐phenyl‐propionic acid (I) and its derivatives, and R (−)‐2‐anilino‐2‐phenyl‐propionic acid (II). The configuration of I was confirmed, that of II established by ORD. measurements, after transformation of the phenyl into cyclohexyl groups. On a palladium catalyst the hydrogenolysis of I, its methyl and ethyl esters and its amide proceeded with 72 to 99% inversion of configuration, that of II with at least 66% inversion. The ester of the quaternary ammonium derivative of I gave as much inversion as retention (= racemisation).