Asymmetric synthesis of (S)-ibuprofen by esterification with amides of (S)-lactic acid as chiral auxiliaries:: experimental and theoretical results
Asymmetric synthesis of (S)-ibuprofen by esterification with amides of (S)-lactic acid as chiral auxiliaries:: experimental and theoretical results
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DOI：
10.1016/s0040-4039(02)00792-x
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发表时间：
2002-06-10
影响因子：
1.8
通讯作者：
Tricca, ML
中科院分区：
文献类型：
--
作者：
Ammazzalorso, A;Amoroso, R;Tricca, ML
介绍了一种新的手性布洛芬的动态动力学分解合成方法。以双环己基碳二亚胺（DCC）和4-二甲氨基吡啶（DMAP）为缩合剂，以(S)-乳酸酰胺为手性助剂，将外消旋布洛芬转化为相应的酯类非对映体混合物。该反应主要产生两种非对映体中的一种，具有良好的非对映体比例。通过分子力学计算，利用MM2力场探讨了立体选择性的原因。(C) 2002 Elsevier Science Ltd.版权所有。
A novel synthesis of chiral ibuprofen by a dynamic kinetic resolution process is described. The racemic ibuprofen was converted into the corresponding diastereomeric mixtures of esters with amides of (S)-lactic acid as chiral auxiliaries, using dicyclohexylcarbodiimide (DCC) and 4-dimethylaminopyridine (DMAP) as condensation agents. The reactions afforded predominantly one of the two diastereomers with good diastereomeric ratios. The reasons of the stereoselectivity were also investigated by molecular mechanic calculations, using MM2 force fields. (C) 2002 Elsevier Science Ltd. All rights reserved.