Oxidation Kinetics Resolution of Racemic Aromatic Sulfoxides by Chiral Porphyrin-Inspired N4 Ligand with Manganese Complex

doi:10.6023/cjoc201805034

	Oxidation Kinetics Resolution of Racemic Aromatic Sulfoxides by Chiral Porphyrin-Inspired N4 Ligand with Manganese Complex
	Li Guosong 2; Lu Chengwei 1; An Yue 1; Gao Shuang 2; Yang Jinchuang 1,2
刊名	CHINESE JOURNAL OF ORGANIC CHEMISTRY
	2018-11-25
卷号	38 期号:11 页码:3070-3077
关键词	ligand N-4 manganese oxidative kinetic resolution aromatic sulfoxides sulfone
ISSN号	0253-2786
DOI	10.6023/cjoc201805034
通讯作者	An Yue(anyue_11@163.com) ; Gao Shuang(sgao@dicp.ac.cn)
英文摘要	Oxidative kinetics resolution of racemic aromatic sulfoxide was studied by using chiral porphyrin-inspired N-4 ligands and manganese in situ complex as catalyst, environment-friendly H2O2 as oxidant and adamantanecarboxvlic acid as additive. The arylalkyl and arylbenzyl sulfoxide substrates were extended by this catalytic system. A maximum Yield of chiral sulfoxide was 40% and the enantioselectivity was 100%. In the meantime, the yield of sulfone a further oxidation products of sulfoxide, was up to 72%. It was found that the catalytic oxidation system is more prone to electron-rich sulfoxide through the competition experiment between electron-rich sulfoxide and electron-deficient sulfoxide substrates. In addition, the success of gram-scale oxidation kinetic resolution also shows that this method has a certain practical value in methodology.
资助项目	National Natural Science Foundation of China[21403100] ; Education Research Program of the Education Department of Liaoning Province[L2014421]
WOS关键词	EFFICIENT ASYMMETRIC OXIDATION ; CATALYZED OXIDATION ; ENANTIOSELECTIVE SULFOXIDATION ; SULFIDE OXIDATION ; HYDROGEN-PEROXIDE ; EPOXIDATION ; SULFONES ; SYSTEM ; YIELDS ; H2O2
WOS研究方向	Chemistry
语种	英语
出版者	SCIENCE PRESS
WOS记录号	WOS:000452171800020
资助机构	National Natural Science Foundation of China ; National Natural Science Foundation of China ; Education Research Program of the Education Department of Liaoning Province ; Education Research Program of the Education Department of Liaoning Province ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; Education Research Program of the Education Department of Liaoning Province ; Education Research Program of the Education Department of Liaoning Province ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; Education Research Program of the Education Department of Liaoning Province ; Education Research Program of the Education Department of Liaoning Province ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; Education Research Program of the Education Department of Liaoning Province ; Education Research Program of the Education Department of Liaoning Province
内容类型	期刊论文
源URL	[http://cas-ir.dicp.ac.cn/handle/321008/166430]
专题	大连化学物理研究所_中国科学院大连化学物理研究所
通讯作者	An Yue; Gao Shuang
作者单位	1.Chinese Acad Sci, Dalian Inst Chem Phys, Dalian Natl Lab Clean Energy, Dalian 116023, Peoples R China 2.Liaoning Normal Univ, Coll Chem & Chem Engn, Dalian 116029, Peoples R China
推荐引用方式 GB/T 7714	Li Guosong,Lu Chengwei,An Yue,et al. Oxidation Kinetics Resolution of Racemic Aromatic Sulfoxides by Chiral Porphyrin-Inspired N4 Ligand with Manganese Complex[J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY,2018,38(11):3070-3077.
APA	Li Guosong,Lu Chengwei,An Yue,Gao Shuang,&Yang Jinchuang.(2018).Oxidation Kinetics Resolution of Racemic Aromatic Sulfoxides by Chiral Porphyrin-Inspired N4 Ligand with Manganese Complex.CHINESE JOURNAL OF ORGANIC CHEMISTRY,38(11),3070-3077.
MLA	Li Guosong,et al."Oxidation Kinetics Resolution of Racemic Aromatic Sulfoxides by Chiral Porphyrin-Inspired N4 Ligand with Manganese Complex".CHINESE JOURNAL OF ORGANIC CHEMISTRY 38.11(2018):3070-3077.