Enantioselective hydrogenation of functionalized olefins catalyzed by Rh-chiral bidentatephosphite complexes
文献类型：期刊论文
| 作者 | 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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| 刊名 | Tetrahedron: Asymmetry
 |
| 出版日期 | 2013 |
| 卷号 | 24期号:2-3页码:104-107 |
| ISSN号 | 0957-4166 |
| 通讯作者 | 王来来 |
| 英文摘要 | 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. |
| 学科主题 | 物理化学与绿色催化 |
| 收录类别 | SCI |
| 资助信息 | the National Natural Science Foundation of China (NSFC 20673130;20773147;21073211;21174155) |
| 语种 | 英语 |
| WOS记录号 | WOS:000315550900003 |
| 公开日期 | 2013-12-03 |
| 源URL | [http://210.77.64.217/handle/362003/4283]  |
| 专题 | 兰州化学物理研究所_OSSO国家重点实验室 |
| 通讯作者 | Wang LL(王来来) |
| 作者单位 | 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 |
| 推荐引用方式 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. |
入库方式： OAI收割
来源：兰州化学物理研究所
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