| Efficient novel 1,2-diphosphite ligands derived from D-mannitol in the Pd-catalyzed asymmetric allylic alkylation | |
| Department | OSSO国家重点实验室 |
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)
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| 2014 | |
| Source Publication | Tetrahedron
 |
| ISSN | 0040-4020 |
| Volume | 70Issue:46Pages:8822-8828 |
| Abstract | 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. |
| Keyword | D-mannitol 1 Palladium Salt 2-diphosphite Ligands Allylic Alkylation |
| Subject Area | 物理化学与绿色催化 |
| DOI | 10.1016/j.tet.2014.10.011 |
| Funding Organization | the National Natural Science Foundation of China (NSFC 20673130;20773147;21073211;21174155) |
| Indexed By | SCI |
| If | 2.641 |
| 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/362003/6584 |
| 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.Chinese Acad Sci, Grad Univ, Beijing 100039, Peoples R China |
| Recommended Citation 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.(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. |
| Files in This Item: | ||||||
| File Name/Size | DocType | Version | Access | License | ||
| 1-s2.0-S004040201401（588KB） | 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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