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Reactions of nitrogen compounds with ruthenium tetroxide. Determination of the absolute configuration of 3‐ethylpiperidine
Author(s) -
Morlacchi Flaviano,
Losacco Vincenzo,
Tortorella Vincenzo
Publication year - 1979
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570160220
Subject(s) - chemistry , methylene , nitrogen atom , nitrogen , ruthenium , absolute configuration , medicinal chemistry , polymer chemistry , organic chemistry , photochemistry , stereochemistry , group (periodic table) , catalysis
(‐)‐3‐Kthylpiperidine and (R)‐(‐)‐2‐ethylglutarie acid have been chemically correlated through N ‐subslituted α‐ethylglutarimides obtained from the oxidation of optically active N ‐ethyl‐ and N ‐benzyl‐3‐ethylpiperidine with ruthenium tetroxide. The (R)‐(‐) configuration of (‐)‐3‐ethylpiperidine was confirmed by CD measurements. The selective oxidation of endocyclic methylenes linked to the nitrogen atom was explained in term of different conformational freedom of endo‐ and exocyclic methylene groups.