| Synthesis of diphosphite ligands derived from glucopyranoside and their application in the Cu-catalyzed asymmetric 1,4-addition of organozinc to enones | |
| Department | 羰基合成与选择氧化国家重点实验室 |
Zhao QL(赵庆鲁); Man Kin Tse; Wang LL(王来来) ; Xing AP(邢爱萍); Jiang XX(蒋先兴)
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| 2010 | |
| Source Publication | Tetrahedron: Asymmetry
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| ISSN | 0957-4166 |
| Volume | 21Pages:2788-2793 |
| Abstract | Novel chiral diphosphite ligands derived from glucopyranoside and H8-binaphthol were synthesized, and successfully employed in the Cu-catalyzed asymmetric 1,4-addition of organozinc reagents dimethylzinc, diethylzinc, and diphenylzinc to cyclic and acyclic enones with up to 96% ee. The stereochemically matched combination of D-glucopyranoside backbone and (R)-H8-binaphthyl in the ligand 2,4-bis{[(R)-1,10-H8-binaphthyl-2,20-diyl] phosphite}-phenyl 3,6-anhydro-b-D-glucopyranoside was essential for inducing high enantioselectivity. A significant dependence of stereoselectivity on the type of enones and the ring size of cyclic enones was observed. Moreover, the sense of the enantiodiscrimination of the products was mainly determined by the configuration of the H8-binaphthyl moieties. |
| Subject Area | 有机功能材料 |
| Funding Organization | the National Natural Science Foundation of China (Nos. 20343005;20473107;20673130;20773147) |
| Indexed By | SCI |
| Language | 英语 |
| Funding Project | 金属有机与超分子催化研究组 |
| Citation statistics | |
| Document Type | 期刊论文 |
| Identifier | http://ir.licp.cn/handle/362003/516 |
| Collection | 羰基合成与选择氧化国家重点实验室（OSSO） |
| Corresponding Author | Man Kin Tse; Wang LL(王来来) |
| Recommended Citation GB/T 7714 | Zhao QL,Man Kin Tse,Wang LL,et al. Synthesis of diphosphite ligands derived from glucopyranoside and their application in the Cu-catalyzed asymmetric 1,4-addition of organozinc to enones[J]. Tetrahedron: Asymmetry,2010,21:2788-2793. |
| APA | 赵庆鲁,Man Kin Tse,王来来,邢爱萍,&蒋先兴.(2010).Synthesis of diphosphite ligands derived from glucopyranoside and their application in the Cu-catalyzed asymmetric 1,4-addition of organozinc to enones.Tetrahedron: Asymmetry,21,2788-2793. |
| MLA | 赵庆鲁,et al."Synthesis of diphosphite ligands derived from glucopyranoside and their application in the Cu-catalyzed asymmetric 1,4-addition of organozinc to enones".Tetrahedron: Asymmetry 21(2010):2788-2793. |
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