| 含金刚烷基团的新型手性单齿亚磷酸酯配体的合成及其在不对称1,4-共轭加成反应中的应用 |
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| 引用本文： | 万博,邝福儿,王来来,徐立进,赵庆鲁,邢爱萍. 含金刚烷基团的新型手性单齿亚磷酸酯配体的合成及其在不对称1,4-共轭加成反应中的应用[J]. 催化学报, 2011, 32(1): 80-85. DOI: 10.1016/S1872-2067(10)60164-7 |
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| 作者姓名： | 万博 邝福儿 王来来 徐立进 赵庆鲁 邢爱萍 |
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| 作者单位： | 中国科学院兰州化学物理研究所羰基合成与选择氧化国家重点实验室,甘肃兰州,730000;香港理工大学应用生物及化学科技学系手性药物合成与开发开放实验室,香港九龙;中国人民大学化学系,北京,100049 |
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| 基金项目： | Supported by the National Natural Science Foundation of China (20343005,20473107,20673130,20773147) |
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| 摘 要： | 以轴手性的BINOL/H8-BINOL(BINOL为联苯酚)和大位阻的金刚烷酰氯为原料,合成了系列新型手性单齿亚磷酸酯配体,并应用于Cu催化的二乙基锌对环烯酮的不对称1,4.共轭加成反应中.结果表明,配体结构中部分氢化的2,2'-(1,1'-联萘基)亚磷酸酯单元和金刚烷基团,有助于改善反应的对映选择性,对映选择性最高可...
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| 关 键 词： | 不对称1 4-共轭加成 单齿亚磷酸酯配体 铜盐 环烯酮 金刚烷 氢八联萘酚单元 |
| 收稿时间： | 2010-07-11 |
New Chiral Monophosphite Ligands Containing BINOL and/or H_8-BINOL Bearing Adamantyl Substituents:Effect of Ligand Scaffold on the Enantioselective 1,4-Conjugate Addition of Diethylzinc to Cyclic Enones |
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| WAN Bo,KWONG Fuk Yee,WANG Lailai,XU Lijin,ZHAO Qinglu,XING Aiping. New Chiral Monophosphite Ligands Containing BINOL and/or H_8-BINOL Bearing Adamantyl Substituents:Effect of Ligand Scaffold on the Enantioselective 1,4-Conjugate Addition of Diethylzinc to Cyclic Enones[J]. Chinese Journal of Catalysis, 2011, 32(1): 80-85. DOI: 10.1016/S1872-2067(10)60164-7 |
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| Authors: | WAN Bo KWONG Fuk Yee WANG Lailai XU Lijin ZHAO Qinglu XING Aiping |
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| Affiliation: | 1State Key Laboratory for Oxo Synthesis & Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, Gansu, China; 2Open Laboratory of Chirotechnology of the Institute of Molecular Technology for Drug Discovery and Synthesis, Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Kowloon, Hong Kong, China; 3Department of Chemistry, Renmin University of China, Beijing 100049, China |
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| Abstract: | A series of new bulky monophosphite ligands were synthesized from axially chiral BINOL/H8-BINOL (BINOL: 1-(2-hydroxynaphthalen-1-yl)naphthalen-2-ol) and highly sterically hindered adamantylcarbonyl chloride. The effectiveness of these ligands was evaluated by the Cu-catalyzed asymmetric 1,4-conjugate addition of diethylzinc to cyclic enones with enantioselectivities of up to 79% ee. The results showed that a ligand structure comprising a partially hydrogenated 2,2′-(1,1′-binaphthyl)phosphite scaffold and an adamantyl moiety was effective in improving the enantioselectivity. |
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| Keywords: | enantioselective 1,4-conjugate addition phosphite ligand copper salt cyclic enone adamantyl H8-binaphtyl |
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