Observations on the Modified Wenker Synthesis of Aziridines and the Development of a Biphasic System

This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://dx.doi.org/10.1021/jo302615gA cheap and reliable process for the modified Wenker cyclization to afford aziridines has been achieved using biphasic conditions for a range of amino alcohol starting materials. A 100 mmol “one-pot” process has also been devised and enantiopurity of the starting amino alcohol is retained in the aziridine product

Formation of 1H-Aziridines from Chalcones and Hydroxylamine

Highly substituted chalcones 1 do not react with two molecules of hydroxylamine affording dioximes 2 or hydroxyamino-oximes 3 as expected according to von Auwers' procedure1): only one molecule of hydroxylamine is consumed leading to trans-configurated 2-benzoyl-3-phenyl-1H-aziridines 4. Aus den hochsubstituierten Chalkonen 1 entstehen nicht die nach von Auwers1) zu erwartenden Dioxime 2 oder Hydroxyamino-oxime 3 unter Verbrauch von zwei Mol Hydroxylamin. Stattdessen wird nur ein Mol Hydroxylamin verbraucht, und es entstehen trans-konfigurierte 2-Benzoyl- 3-phenyl-1H-aziridine 4