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Über die Stereochemie der Hydrogenolyse von N‐Benzyl‐Bindungen II. Die Deuteriolyse von chiralem N,N‐Dimethyl‐phenylglycin und die Konfiguration von (+)‐Phenyl‐essigsäure‐2‐d 1
Author(s) -
Dahn H.,
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.19700530617
Subject(s) - chemistry , phenylacetic acid , benzylamine , hydrogenolysis , phenylacetate , catalytic hydrogenation , steric effects , cleavage (geology) , medicinal chemistry , stereochemistry , catalysis , organic chemistry , biochemistry , geotechnical engineering , fracture (geology) , engineering
The steric course of the hydrogenolytic cleavage of benzyl‐N‐bonds using Pd‐C catalyst was determined by deuteriolysis of R (−)‐N,N‐dimethyl‐phenylglycine I, which gave (+)‐phenylacetic acid containing 70% of the monodeutero compound. The configuration of (+)‐phenylacetic acid‐2‐d 1 was determined ( S ) and its optical purity estimated by Schmidt degradation to chiral S (+)‐benzylamine‐α‐d 1 . On the basis of these results, hydrogenolysis of I can be evaluated to proceed by 80% inversion and 20% retention of configuration. Methyl N,N‐dimethyl‐phenyl‐glycinate yielded racemized methyl phenylacetate‐2‐d 1 .