DICP OpenIR
Oxidation Kinetics Resolution of Racemic Aromatic Sulfoxides by Chiral Porphyrin-Inspired N4 Ligand with Manganese Complex
Yang Jinchuang1,2; Li Guosong2; Lu Chengwei1; An Yue1; Gao Shuang2
Corresponding AuthorAn Yue(anyue_11@163.com) ; Gao Shuang(sgao@dicp.ac.cn)
Keywordligand N-4 manganese oxidative kinetic resolution aromatic sulfoxides sulfone
Source PublicationCHINESE JOURNAL OF ORGANIC CHEMISTRY
2018-11-25
ISSN0253-2786
DOI10.6023/cjoc201805034
Volume38Issue:11Pages:3070-3077
Funding ProjectNational Natural Science Foundation of China[21403100] ; Education Research Program of the Education Department of Liaoning Province[L2014421]
Funding OrganizationNational 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
WOS SubjectChemistry, Organic
WOS Research AreaChemistry
WOS KeywordEFFICIENT ASYMMETRIC OXIDATION ; CATALYZED OXIDATION ; ENANTIOSELECTIVE SULFOXIDATION ; SULFIDE OXIDATION ; HYDROGEN-PEROXIDE ; EPOXIDATION ; SULFONES ; SYSTEM ; YIELDS ; H2O2
AbstractOxidative 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.
Language英语
Funding OrganizationNational 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
WOS IDWOS:000452171800020
PublisherSCIENCE PRESS
Citation statistics
Document Type期刊论文
Identifierhttp://cas-ir.dicp.ac.cn/handle/321008/166431
Collection中国科学院大连化学物理研究所
Corresponding AuthorAn Yue; Gao Shuang
Affiliation1.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
Recommended Citation
GB/T 7714
Yang Jinchuang,Li Guosong,Lu Chengwei,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 Yang Jinchuang,Li Guosong,Lu Chengwei,An Yue,&Gao Shuang.(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 Yang Jinchuang,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.
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