Dipeptides containing D-serine or D-isoserine from the same (R)-aziridine-2-imide by a simple reversal of the synthetic procedure

被引：14

作者：

Cardillo, G

Gentilucci, L

Tolomelli, A

机构：

[1] Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy

[2] CNR, Ctr Studio Fis Macromol, I-40126 Bologna, Italy

来源：

TETRAHEDRON | 1999年 / 55卷 / 52期

关键词：

amino acids; aziridines; oxazolines; rearrangements; regiocontrol;

D O I：

10.1016/S0040-4020(99)00989-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The ring expansion of 3-unsubstituted (R)-aziridine-2-imide-containing dipeptide under acidic conditions gives rise to oxazoline-5-imide regio and stereoselectively, which can be hydrolysed to the dipeptide containing D-isoserine. On the other hand, the ring opening of 3-unsubstituted (R)-aziridine-2-ester dipeptide, easily obtained from the same (R)-aziridine, gives the regioisomeric dipeptide containing D-serine. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：15151 / 15158

页数：8

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