58372-61-5Relevant academic research and scientific papers
ASYMMETRICAL NONBRIDGEHEAD NITROGEN-XXIV. COMPLETE SEPARATION INTO ANTIPODES AND ABSOLUTE CONFIGURATION OF CHIRALIC N-ALKOXYAZIRIDINES
Rudchenko, Vladimir F.,D'yachenko, Oleg A.,Zolotoi, Aleksandr B.,Atovmyan, Lev O.,Chervin, Ivan I.,Kostyanovsky, Remir G.
, p. 961 - 975 (1982)
Optically active derivates 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 diamides R-(+2d) and S-(-2f) by chrystallisation from methyllactate; the diamide S(-2g) by asymmetric inversion reaction at the N atom while heating in methyllactate.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) wich under the effect of diazoethane afford diethyl esters R-(+1) and S-(-1) with optical purity of 96.2 and 93.8percent (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 derivates obtained were established.
Asymmetric three-coordinated nitrogen compounds: Spontaneous resolution and absolute asymmetric synthesis
Kostyanovsky, Remir G.,Kostyanovsky, Vasilii R.,Gul'nara K. Kadorkina,Lyssenko, Konstantin A.
, p. 111 - 113 (2003)
The spontaneous resolution of conglomerates of a dibenzo analogue of Tr?ger's base 1 and aziridine 2, as well as the second-order asymmetric transformation of (±)-1 into a single enantiomer were carried out for the first time.
