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 beta-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-like mechanism of the nucleophilic attack were unambiguously identified by the (2R,3S) X-ray absolute configuration determination of enantiomerically pure beta-amino derivative 9, obtained from (2R,3R)-4, and by its chemical correlation with meso alpha,beta-bis[N-(methanesulfonyl)amino]succinate (10).
Stereoselective synthesis of erythro beta-substituted aspartates / Antolini, Luciano; Bucciarelli, Maria; Caselli, Emilia; Davoli, Paolo; Forni, Arrigo; Moretti, Irene; Prati, Fabio; Torre, Giovanni. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - STAMPA. - 62:(1997), pp. 8784-8789.
Stereoselective synthesis of erythro beta-substituted aspartates
ANTOLINI, Luciano;BUCCIARELLI, Maria;CASELLI, Emilia;DAVOLI, Paolo;FORNI, Arrigo;MORETTI, Irene;PRATI, Fabio;TORRE, Giovanni
1997
Abstract
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 beta-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-like mechanism of the nucleophilic attack were unambiguously identified by the (2R,3S) X-ray absolute configuration determination of enantiomerically pure beta-amino derivative 9, obtained from (2R,3R)-4, and by its chemical correlation with meso alpha,beta-bis[N-(methanesulfonyl)amino]succinate (10).Pubblicazioni consigliate
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