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	Highly enantioselective oxidative couplings of 2-naphthols catalyzed by chiral bimetallic oxovanadium complexes with either oxygen or air as oxidant
	Guo, Qi-Xiang; Wu, Zhi-Jun; Luo, Zhi-Bin; Liu, Quan-Zhong; Ye, Jian-Liang; Luo, Shi-Wei; Cun, Lin-Feng; Gong, Liu-Zhu
刊名	Journal of the american chemical society
	2007-11-14
卷号	129期号:45页码:13927-13938
ISSN号	0002-7863
DOI	10.1021/ja074322f
通讯作者	Luo, shi-wei(gonglz@ustc.edu.cn)
英文摘要	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 cid 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 h-8-binaphthol is highly efficient at catalyzing the air-oxidized coupling of 2-naphthols with excellent enantioselectivities of up to 97% ee. v-51 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.
WOS关键词	1,5-DIAZADECALIN METAL-COMPLEXES ; POTENTIAL BASIS-SETS ; ASYMMETRIC CATALYSIS ; RATIONAL DESIGN ; BINAPHTHOL DERIVATIVES ; POLARIZATION FUNCTIONS ; SUBSTITUTED PHENOLS ; VANADIUM COMPLEXES ; FLUORESCENT SENSOR ; SELF-DIMERIZATION
WOS研究方向	Chemistry
WOS类目	Chemistry, Multidisciplinary
语种	英语
出版者	AMER CHEMICAL SOC
WOS记录号	WOS:000250819300041
内容类型	期刊论文
URI标识	http://www.corc.org.cn/handle/1471x/2380279
专题	中国科学院大学
通讯作者	Luo, Shi-Wei
作者单位	1.Chinese Acad Sci, Chengdu Inst Organ Chem, Chengdu 610041, Peoples R China 2.Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, Hefei 230026, Peoples R China 3.Univ Sci & Technol China, Dept Chem, Hefei 230026, Peoples R China 4.Chengdu Inst Chem, Chengdu 610041, Peoples R China 5.Xiamen Univ, Dept Chem, Coll Chem & Chem Engn, Xiamen 361005, Peoples R China 6.Chinese Acad Sci, Grad Sch, Beijing, Peoples R China
推荐引用方式 GB/T 7714	Guo, Qi-Xiang,Wu, Zhi-Jun,Luo, Zhi-Bin,et al. Highly enantioselective oxidative couplings of 2-naphthols catalyzed by chiral bimetallic oxovanadium complexes with either oxygen or air as oxidant[J]. Journal of the american chemical society,2007,129(45):13927-13938.
APA	Guo, Qi-Xiang.,Wu, Zhi-Jun.,Luo, Zhi-Bin.,Liu, Quan-Zhong.,Ye, Jian-Liang.,...&Gong, Liu-Zhu.(2007).Highly enantioselective oxidative couplings of 2-naphthols catalyzed by chiral bimetallic oxovanadium complexes with either oxygen or air as oxidant.Journal of the american chemical society,129(45),13927-13938.
MLA	Guo, Qi-Xiang,et al."Highly enantioselective oxidative couplings of 2-naphthols catalyzed by chiral bimetallic oxovanadium complexes with either oxygen or air as oxidant".Journal of the american chemical society 129.45(2007):13927-13938.

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