Oxidative kinetic resolution of 1-phenylethanol catalyzed by sugar-based salen-Mn(III) complexes
Oxidative kinetic resolution of 1-phenylethanol catalyzed by sugar-based salen-Mn(III) complexes
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DOI：
10.1016/j.carres.2008.04.022
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发表时间：
2008-07-07
影响因子：
3.1
通讯作者：
An, Junwei
中科院分区：
文献类型：
--
作者：
Han, Furong;Zhao, Jiquan;An, Junwei
合成了三种新的手性salen锰（III）配合物，它们在salen配体的水杨醛部分的C-5（5 '）位与糖形成配合物。通过FTIR、MS和元素分析对其结构进行了表征。该配合物与两个已报道的配合物一起被成功地用作手性催化剂，用于1-苯基乙醇的氧化动力学拆分（OKR），使用PhI（OAc）（2）作为氧化剂和KBr作为添加剂。在20 ℃下，在0.5 h内实现了产物的优异的对映体过量（高达89%）。结果表明，配体中水杨醛部分C-5（5 '）位的糖对配合物的催化性能有影响。结果表明，在1-苯基乙醇的OKR反应中，与二亚胺桥旋光方向相同的糖能增强复合物的手性诱导，而与二亚胺桥旋光方向相反的糖则会降低相应复合物的手性诱导. (C)2008爱思唯尔有限公司保留所有权利。
Three new chiral salen-Mn(III) complexes with sugars at the C-5(5') positions of the salicylaldehyde moieties of the salen ligand were synthesized. Their structures were characterized by FTIR, MS, and elemental analysis. The complexes together with two previously reported ones were successfully used as chiral catalysts for the oxidative kinetic resolution (OKR) of 1-phenylethanol using PhI(OAc)(2) as an oxidant and KBr as an additive. Excellent enantiomeric excess (up to 89%) of the product was achieved in 0.5 h at 20 degrees C. The results showed that the sugars at C-5(5') of salicylaldehyde moieties in the ligand had influences on the catalytic performances of the complexes. It was concluded that the sugars with the same rotation direction of polarized light as the diimine bridge within the complex could enhance the chiral induction of the complex in the OKR of 1-phenylethanol, but the sugars with the opposite one would reduce that of the corresponding complex. (C) 2008 Elsevier Ltd. All rights reserved.