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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
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
DOI10.6023/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.
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
WOS类目Chemistry, Organic
语种英语
出版者SCIENCE PRESS
WOS记录号WOS:000452171800020
内容类型期刊论文
URI标识http://www.corc.org.cn/handle/1471x/2372976
专题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
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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