| Polymer-Supported Chiral Monodentate Phosphoramidites in Palladium-Catalyzed Allylic Alkylation Reactions |
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| 作者姓名： | 江志东 孟昭海 |
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| 作者单位： | [1]School of Chemistry and Chemical Engineering, Shanghai Jiaotong University, Shanghai 200240, China [2]Department of Technique Development, SINOPEC Daqing Petrochemical Co. Ltd., Daqing, Heilongjiang 163714, China |
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| 摘 要： | A new and simple method for immobilization of monodentate chiral ligand on the cheap resin has been developed. A series of resin-immobilized phosphoramidite ligands based on BINOL and TADDOL backbones have been synthesized and characterized with gel-phase NMR. The immobilized ligands have been applied to the Pd-catalyzed asymmetric allylic alkylation of 1,3-diphenyl-2-propenyl acetate. Among four ligands, the supported bulky monodentate phosphoramidite ligand based on TADDOL backbone afforded the chiral product with ee up to 65%; moreover, this ligand could be recycled for 3 times without substantial decrease of the conversion and ee.
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| 关 键 词： | 烯丙基烷基化反应 聚合物负载 手性单齿膦配体 钯催化 |
| 修稿时间： | 2006-07-182006-12-15 |
Polymer-Supported Chiral Monodentate Phosphoramidites in Palladium-Catalyzed Allylic Alkylation Reactions |
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| JIANG Zhi-Dong, MENG Zhao-Hai.Polymer-Supported Chiral Monodentate Phosphoramidites in Palladium-Catalyzed Allylic Alkylation Reactions[J].Chinese Journal of Chemistry,2007,25(4):542-545. |
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| Authors: | JIANG Zhi-Dong MENG Zhao-Hai |
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| Institution: | 1.School of Chemistry and Chemical Engineering, Shanghai Jiaotong University, Shanghai 200240, China; 2.Department of Technique Development, SINOPEC Daqing Petrochemical Co. Ltd., Daqing, Heilongjiang 163714, China |
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| Abstract: | A new and simple method for immobilization of monodentate chiral ligand on the cheap resin has been developed. A series of resin-immobilized phosphoramidite ligands based on BINOL and TADDOL backbones have been synthesized and characterized with gel-phase NMR. The immobilized ligands have been applied to the Pd-catalyzed asymmetric allylic alkylation of 1,3-diphenyl-2-propenyl acetate. Among four ligands, the supported bulky monodentate phosphoramidite ligand based on TADDOL backbone afforded the chiral product with ee up to 65%; moreover, this ligand could be recycled for 3 times without substantial decrease of the conversion and ee. |
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| Keywords: | resin supported allylic alkylation catalyst recycle |
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