| Synthesis and Asymmetric Enantioselective Addition of Chiral Polybinaphthyl and Polybinaphthol I.igands |
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| 作者姓名： | 邹小伟 叶怀池 张树伟 刘燕 王春燕 成义祥 |
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| 作者单位： | [1]School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, Jiangsu 210093, China [2]College of Chemical Engineering and Material Science, Zhejang University of Technology, Hangzhou, Zhejiang 310014, China |
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| 基金项目： | Project supported by the National Natural Science Foundation of China （No, 20474028） and Jiangsu Provincial Natural Science Foundation （No BK2004086）. |
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| 摘 要： | Four chiral polymers P-1, P-2, P-3 and P-4 were synthesized by the polymerization of （S）-2,2＇-dioctoxy-1,1＇- binaphthyl-6,6＇-boronic acid （S-M-3） with （S）-6,6＇-dibromo-1,1＇-binaphthol （S-M-1）, （R）-6,6＇-dibromo-1,1＇- binaphthol （R-M-1）, （S）-3,3＇-diiodo-1,1＇-binaphthol （S-M-2） and （R）-3,3＇-diiodo-1,1＇-binaphthol （R-M-2） under Pd-catalyzed Suzuki reaction, respectively. All four polymers can show good solubility in some common solvents due to the nonplanarity of the polymers in the main chain backbone and flexible alkyl groups in the side chain. The analysis results indicate that specific rotation and circular dichroism （CD） spectral signals of the alternative S-S chiral polymers P-1 and P-3 are larger than those of S-R chiral polymers P-2 and P-4, but their UV-Vis and fluorescence spectra are almost similar. The results of asymmetric enantioselectivity of four polymers for diethylzinc addition to benzaldehyde indicate that catalytically active center is （R） or （S）-1, 1＇-binaphthol moieties.
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| 关 键 词： | 不均匀对映有择 铃木联结 联萘酚 高分子材料 苯甲醛 |
| 修稿时间： | 2006-10-082007-03-12 |
Synthesis and Asymmetric Enantioselective Addition of Chiral Polybinaphthyl and Polybinaphthol I.igands |
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| ZOU Xiao-Wei, YE Huai-Chi,ZHANG Shu-Wei, LIU Yan,WANG Chun-Yan, CHENG Yi-Xiang.Synthesis and Asymmetric Enantioselective Addition of Chiral Polybinaphthyl and Polybinaphthol I.igands[J].Chinese Journal of Chemistry,2007,25(7):992-997. |
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| Authors: | ZOU Xiao-Wei YE Huai-Chi ZHANG Shu-Wei LIU Yan WANG Chun-Yan CHENG Yi-Xiang |
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| Institution: | 1. School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, Jiangsu 210093, China ;2. College of Chemical Engineering and Material Science, Zhejang University of Technology, Hangzhou, Zhejiang 310014, China |
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| Abstract: | Four chiral polymers P ‐ 1 , P ‐ 2 , P ‐ 3 and P ‐ 4 were synthesized by the polymerization of (S)‐2,2′‐dioctoxy‐1,1′‐ binaphthyl‐6,6′‐boronic acid (S‐ M‐3 ) with (S)‐6,6′‐dibromo‐1,1′‐binaphthol (S‐ M ‐ 1 ), (R)‐6,6′‐dibromo‐1,1′‐ binaphthol (R‐ M ‐ 1 ), (S)‐3,3′‐diiodo‐1,1′‐binaphthol (S‐ M ‐ 2 ) and (R)‐3,3′‐diiodo‐1,1′‐binaphthol (R‐ M ‐ 2 ) under Pd‐catalyzed Suzuki reaction, respectively. All four polymers can show good solubility in some common solvents due to the nonplanarity of the polymers in the main chain backbone and flexible alkyl groups in the side chain. The analysis results indicate that specific rotation and circular dichroism (CD) spectral signals of the alternative S‐S chiral polymers P ‐ 1 and P ‐ 3 are larger than those of S‐R chiral polymers P ‐ 2 and P ‐ 4 , but their UV‐Vis and fluorescence spectra are almost similar. The results of asymmetric enantioselectivity of four polymers for diethylzinc addition to benzaldehyde indicate that catalytically active center is (R) or (S)‐1,1′‐binaphthol moieties. |
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| Keywords: | （R）-/（S）-1 1＇-binaphthol Suzuki coupling asymmetric enantioselectivity |
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