Stereoselective synthesis of erythro beta-substituted aspartates

被引：36

作者：

Antolini, L ^{[1
]}

Bucciarelli, M ^{[1
]}

Caselli, E ^{[1
]}

Davoli, P ^{[1
]}

Forni, A ^{[1
]}

Moretti, I ^{[1
]}

Prati, F ^{[1
]}

Torre, G ^{[1
]}

机构：

[1] UNIV MODENA,DIPARTIMENTO CHIM,I-41100 MODENA,ITALY

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 25期

关键词：

D O I：

10.1021/jo971285+

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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).

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页码：8784 / 8789

页数：6

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