Asymmetric Allylic Alkylation and Hydrogenation with Transition Metal Complexes of Diphosphite Ligands Based on (1S,2S)-Trans-1,2-cyclohexanediol | |
Department | OSSO国家重点实验室 |
Pang ZB(逄增波)1,2; Tian M(田密)1,2; Li HF(李海峰)1; Wang LL(王来来)1; Wang LL(王来来) | |
2017 | |
Source Publication | Catalysis Letters |
ISSN | 1011-372X |
Volume | 147Issue:4Pages:893-899 |
Abstract | The preparation of new palladium complexes in situ that were composed of a series of chiral diphosphite ligands, which were derived from (1S,2S)-trans-1,2-cyclohexanediol, have been described. It was found that (1S,2S)-bis[(S)-1,1′-binaphthyl-2,2′-diyl]phosphite-cyclohexanediol was the suitable ligand in the Pd-catalyzed allylic alkylation, and up to 75% ee for (E)-dimethyl 2-(1,3-diphenylallyl)malonate was obtained. In compared with the results of the asymmetric allylic alkylation, (1S,2S)-bis[(R)-1,1′-binaphthyl-2,2′-diyl]phosphite-cyclohexanediol was proved to be the most efficient ligand in the Rh-catalyzed asymmetric hydrogenation of dimethyl itaconate and enamides with up to 99% ee. The stereochemically matched combinations between the diol skeleton and diaryl moieties of the ligands were essential for inducing high enantioselectivities in the two transformations. It was found that the sense of the enantiodiscrimination of the products was mainly determined by the configuration of the binaphthyl phosphite moieties. |
Keyword | Phosphite Ligands Allylic Alkylation Hydrogenation Cyclohexanediol |
Subject Area | 物理化学与绿色催化 |
DOI | 10.1007/s10562-017-1986-8 |
Funding Organization | the National Natural Science Foundation of China (Nos. 20773147;21073211;21174155) |
Indexed By | SCI |
If | 2.799 |
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/362003/21731 |
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.Univ Chinese Acad Sci, Beijing 100039, Peoples R China |
Recommended Citation GB/T 7714 | Pang ZB,Tian M,Li HF,et al. Asymmetric Allylic Alkylation and Hydrogenation with Transition Metal Complexes of Diphosphite Ligands Based on (1S,2S)-Trans-1,2-cyclohexanediol[J]. Catalysis Letters,2017,147(4):893-899. |
APA | Pang ZB,Tian M,Li HF,Wang LL,&王来来.(2017).Asymmetric Allylic Alkylation and Hydrogenation with Transition Metal Complexes of Diphosphite Ligands Based on (1S,2S)-Trans-1,2-cyclohexanediol.Catalysis Letters,147(4),893-899. |
MLA | Pang ZB,et al."Asymmetric Allylic Alkylation and Hydrogenation with Transition Metal Complexes of Diphosphite Ligands Based on (1S,2S)-Trans-1,2-cyclohexanediol".Catalysis Letters 147.4(2017):893-899. |
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