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Über die Stereochemie der Hydrogenolyse von N‐Benzyl‐Bindungen I. Die Hydrogenolyse von Derivaten der 2‐Amino‐2‐phenyl‐propionsäure.
Author(s) -
Dahn H.,
Garbarino J. A.,
O'Murchu C.
Publication year - 1970
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19700530616
Subject(s) - chemistry , hydrogenolysis , palladium , amide , stereochemistry , hemiaminal , catalysis , medicinal chemistry , organic chemistry
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).