Asymmetrical nonbridgehead nitrogen—XXIV: Complete separation into antipodes and absolute configuration of chiralic N-alkoxyaziridines

Optically active derivatives of 1 - methoxyaziridine - 2,2 - dicarboxylic acid have been obtained: the diethyl ester S-(? 1a) by kinetic enrichment under the action of 1-ephedrine; the diamines R-(+2d) and S-(?2f) by crystallization from 1-methyllactate; the diamide S-(?2g) by asymmetric inversion reaction at the N atom while heating in 1-methyllacetate. The basic possibility of 1-alkoxyaziridine reactions with retention of optical activity (ammonolysis and reduction with LAH₄) has been demonstrated for S-(?1a) and R-(+1). 1-Methoxy - aziridine - 2,2 - dicarboxylic acid cis-ethyl ester 4 has been completely separated into antipodes 1R, 2S-(+4) and 1S, 2R-(?4) which under the effect of diazoethane afford diethyl esters R-(+1) and S-(?1) with optical purity of 96.2 and 93.8% (determined by PMR using a chiralic shift-reagent). On the basis of X-ray analysis of monoamides of 1 - methoxyaziridine - 2,2 - dicarboxylic acid ethyl ester and of salt +7 the trans-specificity of ammonolysis and hydrolysis of 1 and the absolute configurations of all the optically active derivatives obtained were established.