STEREOSELECTIVE SYNTHESIS OF ERYTHRO BETA-SUBSTITUTED ASPARTATES

The nucleophilic ring opening of trans-aziridine-2,3-dicarboxylate 1 a nd substituted N-acyl-, N-(methoxycarbonyl)-, and N-(methanesulfonyl)a ziridine-2,3-dicarboxylates 2-4 allows an easy synthetic approach to b eta-hydroxy, beta-amino, beta-(alkylthio), and beta-halogenoaspartates 5-8; in this respect, compounds 2-4 display higher reactivities. The erythro stereochemistry of the synthesized aspartates and the S(N)2-li ke mechanism of the nucleophilic attack were unambiguously identified by the (2R,3S) X-ray absolute configuration determination of enantiome rically pure beta-amino derivative 9, obtained from (2R,3R)-4, and by its chemical correlation with meso alpha,beta-bis[N-(methanesulfonyl)a mino]succinate (10).