Regio- and stereoselective synthesis of constrained enantiomeric β-amino acid derivatives

被引：32
|
作者：
Szakonyi, Zsolt [1 ]
Martinek, Tamas A. [1 ]
Sillanpaa, Reijo [2 ]
Fueloep, Ferenc [1 ]
机构：
[1] Univ Szeged, Inst Pharmaceut Chem, H-6720 Szeged, Hungary
[2] Univ Jyvaskyla, Dept Chem, SF-40351 Jyvaskyla, Finland
来源：
TETRAHEDRON-ASYMMETRY | 2008年 / 19卷 / 19期
关键词：
D O I：
10.1016/j.tetasy.2008.09.026
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Chlorosulfonyl isocyanate addition to (-)- and (+)-apopinene furnished monoterpene-fused beta-lactams in highly regio- and stereospecific reactions. beta-Lactams 5 and 13 exhibited reactivities similar to those of the cycloalkane-fused analogs and were easily converted to the p-amino acid and its protected derivatives. The base-catalyzed isomerization of the cis-amino ester afforded the corresponding trans-amino acid enantiomers in excellent yields. The complete isomerization is explained by the stability difference, which was estimated by ab initio calculations between the cis- and trans-diastereomers. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2296 / 2303
页数：8
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