| Synthesis of novel chiral bidentatephosphite ligands derived from the pyranoside backbone of monosaccharides and their application in the Cu-catalyzed conjugate addition of dialkylzinc 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)
| |
| 2011 | |
| Source Publication | Tetrahedron: Asymmetry
 |
| ISSN | 0957-4166 |
| Volume | 22Pages:1885-1890 |
| Abstract | A series of novel bidentatephosphite ligands, derived from methyl 3,6-anhydro-a-D-glucopyranoside and chlorophosphoric acid diaryl ester, were easily synthesized. These ligands were successfully employed in the Cu-catalyzed asymmetric conjugate 1,4-addition of the organozinc reagents diethylzinc and/or dimethylzinc to enones. The stereochemically matched combination of glucopyranoside and (R)-H8- binaphthyl in ligand 2,4-bis{[(R)-1,10-H8-binaphthyl-2,20-diyl] phosphite}-methyl 3,6-anhydro-a-Dglucopyranoside was essential to afford 85% ee for 3-ethylcyclohexanone with an (S)-configuration in THF, using Cu(OTf)2 as a catalytic precursor. When the reaction was carried out at lower temperatures, changing from 10 to 80 C, a marginal influence of the temperature on the enantioselectivity of the reaction was observed. The presence of the methyl substituent at the 1-position of the glucopyranoside skeleton had a negative effect on the enantioselectivity in the 1,4-addition of ZnEt2 to acyclic enones. |
| Subject Area | 有机功能材料 |
| Funding Organization | the National Natural Science Foundation of China (21172226, 21133011) and the Chinese Academy of Sciences |
| Indexed By | SCI |
| Language | 英语 |
| Funding Project | 有机功能材料研究组 |
| Citation statistics | |
| Document Type | 期刊论文 |
| Identifier | http://ir.licp.cn/handle/362003/348 |
| 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. Synthesis of novel chiral bidentatephosphite ligands derived from the pyranoside backbone of monosaccharides and their application in the Cu-catalyzed conjugate addition of dialkylzinc to enones[J]. Tetrahedron: Asymmetry,2011,22:1885-1890. |
| APA | 赵庆鲁,&王来来.(2011).Synthesis of novel chiral bidentatephosphite ligands derived from the pyranoside backbone of monosaccharides and their application in the Cu-catalyzed conjugate addition of dialkylzinc to enones.Tetrahedron: Asymmetry,22,1885-1890. |
| MLA | 赵庆鲁,et al."Synthesis of novel chiral bidentatephosphite ligands derived from the pyranoside backbone of monosaccharides and their application in the Cu-catalyzed conjugate addition of dialkylzinc to enones".Tetrahedron: Asymmetry 22(2011):1885-1890. |
| Files in This Item: | ||||||
| File Name/Size | DocType | Version | Access | License | ||
| 83-Tetrahedron Asymm（449KB） | 开放获取 | License | View Application Full Text | |||
Items in the repository are protected by copyright, with all rights reserved, unless otherwise indicated.
Edit Comment