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The Origin of Chemical and Configurational Stability of Chiral Nonracemic tert ‐Butyl Aziridinecarboxylate Anions
Author(s) -
Alezra Valérie,
Bonin Martine,
Micouin Laurent,
Policar Clotilde,
Husson HenriPhilippe
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200107)2001:13<2589::aid-ejoc2589>3.0.co;2-y
Subject(s) - chemistry , stereocenter , deprotonation , chemical stability , aziridine , walden inversion , alkylation , nitrogen atom , computational chemistry , nitrogen inversion , medicinal chemistry , stereochemistry , organic chemistry , enantioselective synthesis , nitrogen , ion , ring (chemistry) , catalysis
The origin of good chemical and configurational stability of aziridine ester anions derived from ( R )‐(−)‐phenylglycinol has been investigated. Kinetic acidity seems to play an important role in the deprotonation step and chemical stability of the anionic species. Spectroscopic investigations showed that the good overall retention of configuration was governed by the directing effect of the nitrogen atom, which acts as a stereogenic centre in the alkylation step of the enolate intermediate.