| Synthesis of novel diphosphite ligands derived from D-mannitol and their application in Cu-catalyzed enantioselective conjugate 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); Wang LL(王来来) ; Xing AP(邢爱萍)
| |
| 2010 | |
| Source Publication | Tetrahedron: Asymmetry
 |
| ISSN | 0957-4166 |
| Volume | 21Pages:2993-2998 |
| Abstract | A series of novel chiral diphosphite ligands have been synthesized from D-mannitol derivatives and chlorophosphoric acid diary ester, and were successfully employed in the copper catalyzed enantioselective conjugate addition of organozinc reagents diethylzinc and dimethylzinc to cyclic and acyclic enones. The stereochemically matched combination of D-mannitol and (R)-H8-binaphthyl in ligand 1,2:5,6-di-Oisopropylidene-3,4-bis[(R)-1,10-H8-binaphthyl-2,20-diyl] phosphite-D-mannitol was essential to afford 93% ee for 3-ethylcyclohexanone, 92% ee for 3-ethylcyclopentanone, and 90% ee for 3-ethylcycloheptanone in toluene, using Cu(OTf)2 as a catalytic precursor. The results clearly indicated that the chiral organocopper reagent exhibited high enantioselectivies for cyclic enones bearing different ring sizes. As for the backbone of this type of ligand, it has been demonstrated that 1,2:5,6-di-O-isopropylidene-D-mannitol was more efficient than 1,2:5,6-di-O-cyclohexylidene-D-mannitol. The sense of the enantiodiscrimination was mainly determined by the configuration of the diaryl phosphite moieties in the 1,4-addition of cyclic enones. |
| Subject Area | 有机功能材料 |
| Funding Organization | the National Natural Science Foundation of China (NSFC 20343005, 20473107, 20673130, 20773147, and 21073211) |
| Indexed By | SCI |
| Language | 英语 |
| Funding Project | 金属有机与超分子催化研究组 |
| Document Type | 期刊论文 |
| Identifier | http://ir.licp.cn/handle/362003/517 |
| Collection | 羰基合成与选择氧化国家重点实验室（OSSO） |
| Corresponding Author | Wang LL(王来来) |
| Recommended Citation GB/T 7714 | Zhao QL,Wang LL,Xing AP. Synthesis of novel diphosphite ligands derived from D-mannitol and their application in Cu-catalyzed enantioselective conjugate addition of organozinc to enones[J]. Tetrahedron: Asymmetry,2010,21:2993-2998. |
| APA | 赵庆鲁,王来来,&邢爱萍.(2010).Synthesis of novel diphosphite ligands derived from D-mannitol and their application in Cu-catalyzed enantioselective conjugate addition of organozinc to enones.Tetrahedron: Asymmetry,21,2993-2998. |
| MLA | 赵庆鲁,et al."Synthesis of novel diphosphite ligands derived from D-mannitol and their application in Cu-catalyzed enantioselective conjugate addition of organozinc to enones".Tetrahedron: Asymmetry 21(2010):2993-2998. |
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| 9B_Tetrahedron Asymm（573KB） | 开放获取 | License | View Application Full Text | |||
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