Efficient novel 1,2-diphosphite ligands derived from D-mannitol in the Pd-catalyzed asymmetric allylic alkylation
文献类型：期刊论文
| 作者 | Xing AP(邢爱萍)1,2; Pang ZB(逄增波)1,2 ; Li HF(李海峰)1; Wang LL(王来来)1; Wang LL(王来来); Wang LL(王来来)
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| 刊名 | Tetrahedron
 |
| 出版日期 | 2014 |
| 卷号 | 70期号:46页码:8822-8828 |
| 关键词 | 1 D-Mannitol Palladium salt Allylic alkylation 2-Diphosphite ligands |
| ISSN号 | 0040-4020 |
| 通讯作者 | 王来来 |
| 英文摘要 | A novel Pd/1,2-diphosphite catalyzed asymmetric allylic alkylation of 1,3-diarylpropenyl acetate with malonates was developed. Catalyst optimization via a variation in the protecting groups at the 1,2- and/or 5,6-positions of D-mannitol skeleton and in biaryl moieties of the ligands led to a ‘lead’ catalyst, which efficiently mediated the allylic alkylations. The activities and enantioselectivities of the reaction clearly showed that the stereogenic centers of the skeleton and the axially chiral diaryl moieties of the ligands had a synergic effect. The ligand 1,2:5,6-di-O-isopropylidene-3,4-bis[(S)-1,1′-binaphthyl-2,2′-diyl]phosphite-D-mannitol afforded excellent yields (up to 99%) and high levels of enantioselectivies (ee up to 98%) in 1,4-dioxane/CH2Cl2 mixture (v/v, 1:1) using [Pd(π-allyl)Cl]2 as catalytic precursor and LiOAc as base. Dramatic changes in the sense and in the degree of the enantioselectivity depending on the configuration of the diaryl moieties of the ligands and reaction conditions were observed. |
| 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:000344204700003 |
| 公开日期 | 2014-10-23 |
| 源URL | [http://210.77.64.217/handle/362003/6584]  |
| 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); 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.Chinese Acad Sci, Grad Univ, Beijing 100039, Peoples R China |
| 推荐引用方式 GB/T 7714 | Xing AP,Pang ZB,Li HF,et al. Efficient novel 1,2-diphosphite ligands derived from D-mannitol in the Pd-catalyzed asymmetric allylic alkylation[J]. Tetrahedron,2014,70(46):8822-8828. |
| APA | Xing AP,Pang ZB,Li HF,Wang LL,王来来,&王来来.(2014).Efficient novel 1,2-diphosphite ligands derived from D-mannitol in the Pd-catalyzed asymmetric allylic alkylation.Tetrahedron,70(46),8822-8828. |
| MLA | Xing AP,et al."Efficient novel 1,2-diphosphite ligands derived from D-mannitol in the Pd-catalyzed asymmetric allylic alkylation".Tetrahedron 70.46(2014):8822-8828. |
入库方式： OAI收割
来源：兰州化学物理研究所
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