Synthesis and enantioselectivities of soluble polymers incorporating optically active binaphthyl and binaphthol
Synthesis and enantioselectivities of soluble polymers incorporating optically active binaphthyl and binaphthol
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DOI：
10.1002/app.26523
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发表时间：
2007-10
影响因子：
3
通讯作者：
X. Zou;Shuwei Zhang;Yixiang Cheng;Yan Liu;Hui Huang;Chun-Yan Wang
中科院分区：
文献类型：
--
作者：
X. Zou;Shuwei Zhang;Yixiang Cheng;Yan Liu;Hui Huang;Chun-Yan Wang
在Pd催化的Suzuki反应中，通过（S）-6，6 ′-二溴-3，3 ′-双-1，1 ′-联萘与（S）-2，2 ′-二甲氧基-1，1 ′-联萘-6，6 ′-硼酸的聚合合成了聚合物（P-1），并且通过（S）-6，6 ′-二溴-3，3 ′-双-1，1 ′-联萘与（S）-6，6 ′-二乙炔基-2-甲基-2，2 ′-二氧代-1，1 ′-联萘的聚合合成了另一种聚合物（P-2），Pd催化的Sonogashira反应中的2′-二甲氧基-1，1 ′-联萘这两种聚合物在一些常用溶剂中表现出良好的溶解性，并通过NMR、傅里叶变换红外光谱、凝胶渗透色谱和圆二色谱进行了表征。研究了手性单体和聚合物在二乙基锌与苯甲醛不对称加成反应中的应用。结果表明，P-1、P-2和单体（S）-3，3 ′-双-1，1 ′-联萘是二乙基锌与苯甲醛不对称加成反应的有效配体.手性聚合物配体P-1和P-2比它们的单体形式（S）-3，3 ′-双-1，1 ′-联萘更有效，并且可以容易地回收和重复使用而不损失催化活性或对映选择性。© 2007威利期刊公司应用聚合物科学杂志，2007年
A polymer (P-1) was synthesized through the polymerization of (S)-6,6′-dibromo-3,3′-dibutyl-1,1′-binaphthol with (S)-2,2′-dioctoxy-1,1′-binaphthyl-6,6′-boronic acid in a Pd-catalyzed Suzuki reaction, and another polymer (P-2) was synthesized through the polymerization of (S)-6,6′-dibromo-3,3′-dibutyl-1,1′-binaphthol with (S)-6,6′-diethynyl-2,2′-dioctoxy-1,1′-binaphthyl in a Pd-catalyzed Sonogashira reaction. The two polymers showed good solubility in some common solvents and were characterized with NMR, Fourier transform infrared, gel permeation chromatography, and circular dichroism spectroscopy. The application of the chiral monomers and polymers in the asymmetric addition of diethyl zinc to benzaldehyde was studied. The results indicated that P-1, P-2, and the monomer (S)-3,3′-dibutyl-1,1′-binaphthol were efficient ligands in the asymmetric addition of diethyl zinc to benzaldehyde. The chiral polymer ligands P-1 and P-2 were more efficient than their monomeric version, (S)-3,3′-dibutyl-1,1′-binaphthol, and could be easily recovered and reused without a loss of catalytic activity or enantioselectivity. © 2007 Wiley Periodicals, Inc. J Appl Polym Sci, 2007