Asymmetric synthesis of esomeprazole

被引：244
|
作者：
Cotton, H
Elebring, T
Larsson, M
Li, L
Sörensen, H
von Unge, S [1 ]
机构：
[1] AstraZeneca R&D Molndal, Med Chem, S-43183 Molndal, Sweden
[2] AstraZeneca Proc R&D Sodertalje, Proc Chem, S-15185 Sodertalje, Sweden
来源：
TETRAHEDRON-ASYMMETRY | 2000年 / 11卷 / 18期
关键词：
D O I：
10.1016/S0957-4166(00)00352-9
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
A highly efficient synthesis of esomeprazole-the (S)-enantiomer of omeprazole-via asymmetric oxidation of prochiral sulphide 1 is described. The asymmetric oxidation was achieved by titanium-mediated oxidation with cumene hydroperoxide (CHP) in the presence of (S,S)-diethyl tartrate [(S,S)-DET]. The enantioselectivity was provided by preparing the titanium complex in the presence of 1 at an elevated temperature and/or during a prolonged preparation time and by performing the oxidation of 1 in the presence of an amine. An enantioselectivity of >94% ee was obtained using this method. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：3819 / 3825
页数：7
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