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Asymmetric Synthesis of Chiral Heterocyclic Amino Acids via the Alkylation of the Ni(II) Complex of Glycine and Alkyl Halides

文献类型：期刊论文

作者Chen, Hui1,2; Wang, Jiang1; Zhou, Shengbin1; Liu, Hong1
刊名JOURNAL OF ORGANIC CHEMISTRY
出版日期2014-09-05
卷号79期号:17页码:7872-7879
ISSN号0022-3263
DOI10.1021/jo501571j
文献子类Article
英文摘要An investigation into the reactivity profile of alkyl halides has led to the development of a new method for the asymmetric synthesis of chiral heterocyclic amino acids. This protocol involves the asymmetric alkylation of the Ni(II) complex of glycine to form an intermediate, which then decomposes to form a series of valuable chiral amino acids in high yields and with excellent diastereoselectivity. The chiral amino acids underwent a smooth intramolecular cyclization process to afford the valuable chiral heterocyclic amino acids in high yields and enantioselectivities. This result paves the way for the development of a new synthetic method for chiral heterocyclic amino acids.
WOS关键词ANGIOTENSIN-CONVERTING ENZYME ; MICHAEL ADDITION-REACTIONS ; SUBSTITUTED PYROGLUTAMIC ACIDS ; NUCLEOPHILIC GLYCINE ; ENANTIOSELECTIVE SYNTHESIS ; NICKEL(II) GLYCINATE ; FACE DIASTEREOSELECTIVITY ; STEREODIVERGENT SYNTHESIS ; MANNICH REACTIONS ; GENERAL-METHOD
资助项目National Natural Science Foundation of China[21021063] ; National Natural Science Foundation of China[91229204] ; National Natural Science Foundation of China[81302633] ; National Natural Science Foundation of China[81025017] ; National S&T Major Projects - State Key Laboratory of Bioorganic Chemistry[2012ZX09103101-072] ; National S&T Major Projects - State Key Laboratory of Bioorganic Chemistry[2012ZX09301001-005] ; National S&T Major Projects - State Key Laboratory of Bioorganic Chemistry[2013ZX09507-001] ; National S&T Major Projects - State Key Laboratory of Bioorganic Chemistry[2014ZX09507002-001] ; K. C. Wong Education Foundation, Hong Kong[00000000]
WOS研究方向Chemistry
语种英语
WOS记录号WOS:000341345400009
出版者AMER CHEMICAL SOC
源URL[http://119.78.100.183/handle/2S10ELR8/276908]  
专题药物化学研究室
通讯作者Wang, Jiang
作者单位1.Chinese Acad Sci, Shanghai Inst Mat Med, CAS Key Lab Receptor Res, Shanghai 201203, Peoples R China;
2.Nanchang Univ, Coll Pharm, Nanchang 330006, Peoples R China
推荐引用方式
GB/T 7714		 Chen, Hui,Wang, Jiang,Zhou, Shengbin,et al. Asymmetric Synthesis of Chiral Heterocyclic Amino Acids via the Alkylation of the Ni(II) Complex of Glycine and Alkyl Halides[J]. JOURNAL OF ORGANIC CHEMISTRY,2014,79(17):7872-7879.
APA Chen, Hui,Wang, Jiang,Zhou, Shengbin,&Liu, Hong.(2014).Asymmetric Synthesis of Chiral Heterocyclic Amino Acids via the Alkylation of the Ni(II) Complex of Glycine and Alkyl Halides.JOURNAL OF ORGANIC CHEMISTRY,79(17),7872-7879.
MLA Chen, Hui,et al."Asymmetric Synthesis of Chiral Heterocyclic Amino Acids via the Alkylation of the Ni(II) Complex of Glycine and Alkyl Halides".JOURNAL OF ORGANIC CHEMISTRY 79.17(2014):7872-7879.

入库方式： OAI收割

来源：上海药物研究所

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