Highly Enantioselective Oxidative Couplings of 2-NaphtholsCatalyzed by Chiral Bimetallic Oxovanadium Complexes withEither Oxygen or Air as Oxidant
文献类型：期刊论文
| 作者 | Qi-Xiang Guo ; Zhi-Jun Wu ; Zhi-Bin Luo ; Quan-Zhong Liu ; Jian-Liang Ye ; Shi-Wei Luo ; Lin-Feng Cun ; Liu-Zhu Gong |
| 刊名 | Journal of the American Chemical Society
 |
| 出版日期 | 2007 |
| 卷号 | 129期号:45页码:13927-13938 |
| 产权排序 | 3 |
| 通讯作者 | Shi-Wei Luo ; Liu-Zhu Gong |
| 合作状况 | 其它 |
| 中文摘要 | The chiral bimetallic oxovanadium complexes have been designed for the enantioselective oxidative coupling of 2-naphthols bearing various substituents at C6 and/or C7. The chirality transferring from the amino acid to the axis of the biphenyl in oxovanadium complexes 2 was found to occur with the use of UV and CD spectra and DFT calculation. The homo-coupling reaction with oxygen as the oxidant was promoted by 5 mol % of an oxovanadium complex derived from l-isoleucine and achiral biphenol to afford binaphthols in nearly quantitative yields with high enantioselectivities of up to 98% ee. An oxovanadium complex derived from l-isoleucine and H8-binaphthol is highly efficient at catalyzing the air-oxidized coupling of 2-naphthols with excellent enantioselectivities of up to 97% ee. 51V NMR study shows that the oxovanadium complexes have two vanadium(V) species. Kinetic studies, the cross-coupling reaction, and HRMS spectral studies on the reaction have been carried out and illustrate that two vanadium(V) species are both involved in catalysis and that the coupling reaction undergoes a radical−radical mechanism in an intramolecular manner. Quantum mechanical calculations rationalize the importance of the cooperative effects of the axial chirality matching S-amino acids on the stereocontrol of the oxidative coupling reaction. The application of the transformation in the preparation of chiral ligands and conjugated polymers confirms the importance of the current process in organic synthesis. |
| 学科主题 | 天然产物研究 |
| 收录类别 | SCI |
| 语种 | 英语 |
| 公开日期 | 2016-02-26 |
| 源URL | [http://210.75.237.14/handle/351003/26767]  |
| 专题 | 成都生物研究所_天然产物研究 |
| 推荐引用方式 GB/T 7714 | Qi-Xiang Guo,Zhi-Jun Wu,Zhi-Bin Luo,et al. Highly Enantioselective Oxidative Couplings of 2-NaphtholsCatalyzed by Chiral Bimetallic Oxovanadium Complexes withEither Oxygen or Air as Oxidant[J]. Journal of the American Chemical Society,2007,129(45):13927-13938. |
| APA | Qi-Xiang Guo.,Zhi-Jun Wu.,Zhi-Bin Luo.,Quan-Zhong Liu.,Jian-Liang Ye.,...&Liu-Zhu Gong.(2007).Highly Enantioselective Oxidative Couplings of 2-NaphtholsCatalyzed by Chiral Bimetallic Oxovanadium Complexes withEither Oxygen or Air as Oxidant.Journal of the American Chemical Society,129(45),13927-13938. |
| MLA | Qi-Xiang Guo,et al."Highly Enantioselective Oxidative Couplings of 2-NaphtholsCatalyzed by Chiral Bimetallic Oxovanadium Complexes withEither Oxygen or Air as Oxidant".Journal of the American Chemical Society 129.45(2007):13927-13938. |
入库方式： OAI收割
来源：成都生物研究所
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