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

页码：2296 / 2303

页数：8

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