Synthesis of novel cyclohexanediol-derived chiral phosphite ligands and their application in the Cu-catalyzed conjugate addition of organozinc to cyclic enones | |
Department | OSSO国家重点实验室 |
Pang ZB(逄增波)1,2; Li HF(李海峰)1; Wang LL(王来来)1; Wang LL(王来来) | |
2016 | |
Source Publication | Chinese Chemical Letters |
ISSN | 1001-8417 |
Volume | 27Issue:2Pages:271-276 |
Abstract | A series of novel chiral diphosphite ligands have been synthesized from (1R,2R)-trans-1,2-cyclohexanediol, (1S,2S)-trans-1,2-cyclohexanediol, racemic trans-1,2-cyclohexanediol and chlorophosphoric acid diary ester, and were successfully employed in the Cu-catalyzed asymmetric 1,4-conjugate addition of diethylzinc to cyclohexenone with up to 99% ee. It was found that ligand 1,2-bis[(R)-1,1′-binaphthyl-2,2′-diyl]phosphitecyclohexanediol 6a derived from racemic diol skeleton can show similar catalytic performance compared with ligand (1R,2R)-bis[(R)-1,1′-binaphthyl-2,2′-diyl]phosphitecyclohexanediol 6a′ derived from enantiopure starting material. A significant dependence of stereoselectivity on the type of enone and the ring size of the cyclic enone was observed. Moreover, the configuration of the products was mainly determined by the configuration of the binaphthyl moieties of diphosphite ligands in the 1,4-addition of cyclic enones. |
Keyword | Racemic And Chiral Cyclohexanediol Phosphite Ligands Organozinc Cyclic Enones Cu-catalyzed Conjugate Addition |
Subject Area | 物理化学与绿色催化 |
DOI | 10.1016/j.cclet.2015.10.009 |
Funding Organization | the National Natural Science Foundation of China (Nos. 20773147;21073211;21174155) |
Indexed By | SCI |
If | 1.932 |
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/362003/19026 |
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.State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, China 2.University of Chinese Academy of Sciences, Beijing 100039, China |
Recommended Citation GB/T 7714 | Pang ZB,Li HF,Wang LL,et al. Synthesis of novel cyclohexanediol-derived chiral phosphite ligands and their application in the Cu-catalyzed conjugate addition of organozinc to cyclic enones[J]. Chinese Chemical Letters,2016,27(2):271-276. |
APA | Pang ZB,Li HF,Wang LL,&王来来.(2016).Synthesis of novel cyclohexanediol-derived chiral phosphite ligands and their application in the Cu-catalyzed conjugate addition of organozinc to cyclic enones.Chinese Chemical Letters,27(2),271-276. |
MLA | Pang ZB,et al."Synthesis of novel cyclohexanediol-derived chiral phosphite ligands and their application in the Cu-catalyzed conjugate addition of organozinc to cyclic enones".Chinese Chemical Letters 27.2(2016):271-276. |
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