| Enantioselective hydrogenation of functionalized olefins catalyzed by Rh-chiral bidentatephosphite complexes | |
| Department | OSSO国家重点实验室 |
Zhao QL(赵庆鲁)1,2; Miao X(苗晓)1,3; Wang LL(王来来)1 ; Wang LL(王来来)
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| 2013 | |
| Source Publication | Tetrahedron: Asymmetry
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| ISSN | 0957-4166 |
| Volume | 24Issue:2-3Pages:104-107 |
| Abstract | A novel catalytic system for the hydrogenation of dimethyl itaconate has been developed by using rhodium-diphosphite complexes. These chiral diphosphite ligands were derived from glucopyranoside, D-mannitol derivatives, and binaphthyl or H-8-binaphthyl phosphochloridites. The ligands based on the methyl 3,6-anhydro-alpha-D-glucopyranoside backbone and (R)- and (S)-binaphthol and/or (R)- and (S)-2,2'-dihydroxy-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthol gave almost complete conversion of the dimethyl itaconate and both enantiomers of dimethyl 2-methylsuccinate with excellent enantioselectivities. The stereochemically matched combination of methyl 3,6-anhydro-alpha-D-glucopyranoside and H-8-(S)-binaphthyl in ligand 2,4-bis{[(S)-1,1'-H-8-binaphthyl-2,2'-diyl]-phosphite} methyl 3,6-anhydro-alpha-D-glucopyranoside was essential to afford dimethyl 2-methylsuccinate with up to 98% ee. The sense of the enantioselectivity of products was predominantly determined by the configuration of the biaryl moieties of the ligands. An initial screening of [Rh(cod)2]BF4 with these ligands in the hydrogenation of (E)-2-(3-butoxy-4-methoxybenzylidene)-3-methylbutanoic acid was carried out. Good enantioselectivity (75% ee) and low yield for (R)-2-(3-butoxy-4-methoxybenzyl)-3-methylbutanoic acid were obtained. |
| Subject Area | 物理化学与绿色催化 |
| DOI | 10.1016/j.tetasy.2012.12.001 |
| Funding Organization | the National Natural Science Foundation of China (NSFC 20673130;20773147;21073211;21174155) |
| Indexed By | SCI |
| If | 2.165 |
| Language | 英语 |
| Funding Project | 有机功能材料研究组 |
| compositor | 第一作者单位 |
| Citation statistics | |
| Document Type | 期刊论文 |
| Identifier | http://ir.licp.cn/handle/362003/4283 |
| 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) |
| Affiliation | 1.Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China 2.Qilu Branch Co, Res Inst, Sinopec, Zibo 255400, Peoples R China 3.Univ Chinese Acad Sci, Beijing 100039, Peoples R China |
| Recommended Citation GB/T 7714 | Zhao QL,Miao X,Wang LL,et al. Enantioselective hydrogenation of functionalized olefins catalyzed by Rh-chiral bidentatephosphite complexes[J]. Tetrahedron: Asymmetry,2013,24(2-3):104-107. |
| APA | Zhao QL,Miao X,Wang LL,&王来来.(2013).Enantioselective hydrogenation of functionalized olefins catalyzed by Rh-chiral bidentatephosphite complexes.Tetrahedron: Asymmetry,24(2-3),104-107. |
| MLA | Zhao QL,et al."Enantioselective hydrogenation of functionalized olefins catalyzed by Rh-chiral bidentatephosphite complexes".Tetrahedron: Asymmetry 24.2-3(2013):104-107. |
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| Tetrahedron Asymmetr（608KB） | 期刊论文 | 作者接受稿 | 开放获取 | CC BY-NC-SA | View Application Full Text | |
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