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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Optically Pure Aminopolyols and Polyoxamic Acid Derivatives from Aziridine-2-carboxylates

Heribert Dollt and Volker Zabel

Australian Journal of Chemistry 52(4) 259 - 270
Published: 1999

Abstract

Various new chiral building blocks could easily be prepared from optically pure cis and trans ethyl 3-(1′,3′- dioxolan-4′-yl)aziridine-2-carboxylates. A stereochemically pure 1,3-dioxolan in the allyl position of an α-bromoacrylate induced a high (3R*,4′S*) selectivity in the Michael addition with an amine. After oxygen at the inducing centre was exchanged with nitrogen bearing a bulky substituent, the directing influence of this new group was examined. Solvent effects influencing the cis/trans ratio of aziridine formation are discussed.

https://doi.org/10.1071/C98026

© CSIRO 1999

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