Stereoselective Synthesis of Erythro β-Substituted Aspartates

This is the authors' abstract. We don't add key points for this paper.

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