151131-78-1Relevant articles and documents
α-AMINO ACIDS OF THE ADAMANTANE SERIES. IV. STEREOCHEMISTRY OF THE DEM'YANOV REACTION FOR 1-ADAMANTYLGLYCINE AND 1-ADAMANTYLGLYCINE METHYL ESTER
Krasutskii, P. A.,Semenova, I. G.,Safranova, E. E.
, p. 1827 - 1830 (2007/10/02)
The stereochemical features of the deamination of 1-adamantylglycine and its methyl ester in 70percent sulfuric acid by the action of sodium nitrite were investigated.It was shown that the rearrangement of the α-amino acid and α-amino ester is stereospecific, and configurational comparisons indicate frontal attack by the Cα-Cβ bond of the adamantane fragment on the carbocationic center formed as a result of the elimination of a nitrogen molecule.The absolute configuration of the β-hydroxy derivatives of homoadamantane was determind by stereochemical correlation.