The Origin of Chemical and Configurational Stability of Chiral Nonracemic tert-Butyl Aziridinecarboxylate Anions

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...

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Bibliographic Details
Published in:European journal of organic chemistry 2001-07, Vol.2001 (13), p.2589-2594
Main Authors: Alezra, Valérie, Bonin, Martine, Micouin, Laurent, Policar, Clotilde, Husson, Henri-Philippe
Format: Article
Language:English
Subjects:
Aziridine
Chemical Sciences
Configurational stability
Inorganic chemistry
Kinetic acidity
Nitrogen inversion
Quaternary amino esters
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Summary: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.
ISSN:1434-193X
1099-0690
DOI:10.1002/1099-0690(200107)2001:13<2589::AID-EJOC2589>3.0.CO;2-Y