Configurationally Stable (S)- and (R)--Methylproline-Derived Ligands for the Direct Chemical Resolution of Free Unprotected (3)-Amino Acids

doi:10.1002/ejoc.201800120

	Configurationally Stable (S)- and (R)--Methylproline-Derived Ligands for the Direct Chemical Resolution of Free Unprotected (3)-Amino Acids
	Zhou, Shengbin 2,4; Wang, Shuni 2,4; Wang, Jiang2,4 ; Nian, Yong 2,4; Peng, Panfeng 2,4; Soloshonok, Vadim A.1,3; Liu, Hong2,4
刊名	EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
	2018-04-23
期号	15 页码:1821-1832
关键词	Amino acids Chemical resolution Nickel Nonracemizable ligands Antiviral agents
ISSN号	1434-193X
DOI	10.1002/ejoc.201800120
文献子类	Article
英文摘要	Reported herein is a chemical method for the direct resolution of unprotected racemic -substituted--amino acids ((3)-AAs) that uses specially designed, stable, and recyclable -methylproline-derived chiral ligands. The versatility of this methodology is unmatched by biocatalytic approaches. The method shows a broad synthetic generality for various aryl- or alkyl-substituted (3)-AAs, and the new nonracemizable ligands can be accessed readily. Furthermore, the presented method produces an excellent stereochemical outcome and has a fully recyclable source of chirality, and the reaction conditions are operationally simple and convenient. The procedure has also been successfully applied to the scalable synthesis of the anti-HIV drug maraviroc.
资助项目	National Natural Science Foundation of China[81620108027] ; National Natural Science Foundation of China[21632008] ; Major Project of Chinese National Programs for Fundamental Research and Development[2015CB910304]
WOS关键词	BETA-AMINO ACIDS ; DYNAMIC KINETIC RESOLUTION ; NUCLEOPHILIC GLYCINE EQUIVALENTS ; CATALYTIC ASYMMETRIC-SYNTHESIS ; CHIRAL NICKEL(II) GLYCINATE ; ENANTIOMERICALLY PURE FORM ; ALPHA-AMINO ; NI(II) COMPLEXES ; ENANTIOSELECTIVE SYNTHESIS ; BIOMIMETIC TRANSAMINATION
WOS研究方向	Chemistry
语种	英语
出版者	WILEY-V C H VERLAG GMBH
WOS记录号	WOS:000430542500011
内容类型	期刊论文
源URL	[http://119.78.100.183/handle/2S10ELR8/279796]
专题	药物化学研究室
通讯作者	Soloshonok, Vadim A.; Liu, Hong
作者单位	1.Univ Basque Country UPV EHU, Fac Chem, Dept Organ Chem 1, Paseo Manuel Lardizabal 3, San Sebastian 20018, Spain; 2.Univ Chinese Acad Sci, 19A Yuquan Rd, Beijing 100049, Peoples R China; 3.IKERBASQUE Basque Fdn Sci, Maria Diaz de Haro 3, Bilbao 48013, Spain 4.Chinese Acad Sci, CAS Key Lab Receptor Res, Shanghai Inst Mat Med, 555 Zuchongzhi Rd, Shanghai 201203, Peoples R China;
推荐引用方式 GB/T 7714	Zhou, Shengbin,Wang, Shuni,Wang, Jiang,et al. Configurationally Stable (S)- and (R)--Methylproline-Derived Ligands for the Direct Chemical Resolution of Free Unprotected (3)-Amino Acids[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY,2018(15):1821-1832.
APA	Zhou, Shengbin.,Wang, Shuni.,Wang, Jiang.,Nian, Yong.,Peng, Panfeng.,...&Liu, Hong.(2018).Configurationally Stable (S)- and (R)--Methylproline-Derived Ligands for the Direct Chemical Resolution of Free Unprotected (3)-Amino Acids.EUROPEAN JOURNAL OF ORGANIC CHEMISTRY(15),1821-1832.
MLA	Zhou, Shengbin,et al."Configurationally Stable (S)- and (R)--Methylproline-Derived Ligands for the Direct Chemical Resolution of Free Unprotected (3)-Amino Acids".EUROPEAN JOURNAL OF ORGANIC CHEMISTRY .15(2018):1821-1832.