Novel MOP-type H-8-binaphthyl monodentate phosphite ligands and their applications in transition metal-catalyzed asymmetric 1,4-conjugate additions and hydroformylations | |
Department | OSSO国家重点实验室 |
Tian M(田密)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) | |
2017 | |
Source Publication | Tetrahedron: Asymmetry |
ISSN | 0957-4166 |
Volume | 28Issue:2Pages:330-337 |
Abstract | A new series of monodentate phosphites based on the rigid, axially chiral monoesterified H8-BINOL, which are easy to prepare from the readily accessible phosphorylating reagents (Sa)- or (Ra)-1,1′-binaphthyl-2,2′-diylchlorophosphite and (Sa)- or (Ra)-1,1′-H8-binaphthyl-2,2′-diylchlorophosphite, have been synthesized. All ligands were purified on a silica gel column under a nitrogen atmosphere with moderate yields, and were white solids and air-stable at room temperature. These ligands afforded good to excellent enantioselectivities in the Cu-catalyzed 1,4-conjugate addition of 2-cyclohexenone with nucleophiles Et2Zn (96% ee) and with Ph2Zn (65% ee), 2-cyclopentenone with Et2Zn (95% ee), 2-cycloheptenone with Et2Zn (76% ee), and 5,6-dihydro-2H-pyran-2-one with Et2Zn (90% ee). In the Rh-catalyzed asymmetric hydroformylation of styrene, these ligands showed a chemoselectivity of >99% in aldehydes, and a satisfactory branched over linear ratio (96/4). Moreover, the sense of the enantiodiscrimination of the products was mainly determined by the configuration of the BINOL-based or H8-BINOL-based phosphocycle. |
Subject Area | 物理化学与绿色催化 |
DOI | 10.1016/j.tetasy.2017.01.011 |
Funding Organization | the National Natural Science Foundation of China (Nos. 20773147;21073211;21174155;21633013) |
Indexed By | SCI |
If | 2.126 |
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/362003/21616 |
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 | Tian M,Pang ZB,Li HF,et al. Novel MOP-type H-8-binaphthyl monodentate phosphite ligands and their applications in transition metal-catalyzed asymmetric 1,4-conjugate additions and hydroformylations[J]. Tetrahedron: Asymmetry,2017,28(2):330-337. |
APA | Tian M,Pang ZB,Li HF,Wang LL,&王来来.(2017).Novel MOP-type H-8-binaphthyl monodentate phosphite ligands and their applications in transition metal-catalyzed asymmetric 1,4-conjugate additions and hydroformylations.Tetrahedron: Asymmetry,28(2),330-337. |
MLA | Tian M,et al."Novel MOP-type H-8-binaphthyl monodentate phosphite ligands and their applications in transition metal-catalyzed asymmetric 1,4-conjugate additions and hydroformylations".Tetrahedron: Asymmetry 28.2(2017):330-337. |
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