Asymmetric Synthesis of Aromatic and Heteroaromatic -Amino Acids Using a Recyclable Axially Chiral Ligand

doi:10.1002/ejoc.201501442

	Asymmetric Synthesis of Aromatic and Heteroaromatic -Amino Acids Using a Recyclable Axially Chiral Ligand
	Li, Jia1,2 ; Zhou, Shengbin 2; Wang, Jiang2 ; Kawashima, Aki 3; Moriwaki, Hiroki 3; Soloshonok, Vadim A.3,4; Liu, Hong1,2
刊名	EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
	2016-02
期号	5 页码:999-1006
关键词	Axial chirality Ligand design Nickel Amino acids Alkylation Diastereoselectivity
ISSN号	1434-193X
DOI	10.1002/ejoc.201501442
文献子类	Article
英文摘要	In this work, we introduce a new chiral nucleophilic glycine equivalent containing a recyclable axially chiral ligand. As the first synthetic application of this glycine reagent, we describe its alkylation reactions with various alkyl bromides, conducted under unconventional conditions using methanol as the reaction medium. The alkylation products were isolated in diastereomerically pure state in high >80% yields. The wide structural scope of this method and its limitations are convincingly demonstrated and critically discussed. The recyclable nature of the nonracemizable axially chiral ligands together with the generally excellent stereochemical outcome makes this a very valuable method for the practical preparation of enantiomerically pure aromatic tailor-made -amino acids.
资助项目	National Natural Science Foundation of China (NSFC)[21021063] ; National Natural Science Foundation of China (NSFC)[81302633] ; National Natural Science Foundation of China (NSFC)[91229204] ; National High Technology Research and Development Program of China[2012AA020302] ; SA-SIBS Scholarship Program[00000000]
WOS关键词	NUCLEOPHILIC GLYCINE EQUIVALENTS ; MICHAEL ADDITION-REACTIONS ; NI(II) COMPLEXES ; STEREOSELECTIVE-SYNTHESIS ; EFFICIENT SYNTHESIS ; SCHIFF-BASE ; RECEPTOR ANTAGONISTS ; PRACTICAL SYNTHESIS ; PYROGLUTAMIC ACIDS ; KINETIC RESOLUTION
WOS研究方向	Chemistry
语种	英语
出版者	WILEY-V C H VERLAG GMBH
WOS记录号	WOS:000370337700020
内容类型	期刊论文
源URL	[http://119.78.100.183/handle/2S10ELR8/276160]
专题	药物化学研究室药物安全性评价中心国家新药筛选中心
通讯作者	Soloshonok, Vadim A.; Liu, Hong
作者单位	1.China Pharmaceut Univ, Sch Pharm, Nanjing 210009, Jiangsu, Peoples R China; 2.Chinese Acad Sci, Shanghai Inst Mat Med, Key Lab Receptor Res, 555 Zu Chong Zhi Rd, Shanghai 201203, Peoples R China; 3.Univ Basque Country UPV EHU, Fac Chem, Dept Organ Chem 1, Paseo Manuel Lardizabal 3, San Sebastian 20018, Spain; 4.Ikerbasque, Basque Fdn Sci, Alameda Urquijo 36-5,Plaza Bizkaia, E-48011 Bilbao, Spain
推荐引用方式 GB/T 7714	Li, Jia,Zhou, Shengbin,Wang, Jiang,et al. Asymmetric Synthesis of Aromatic and Heteroaromatic -Amino Acids Using a Recyclable Axially Chiral Ligand[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY,2016(5):999-1006.
APA	Li, Jia.,Zhou, Shengbin.,Wang, Jiang.,Kawashima, Aki.,Moriwaki, Hiroki.,...&Liu, Hong.(2016).Asymmetric Synthesis of Aromatic and Heteroaromatic -Amino Acids Using a Recyclable Axially Chiral Ligand.EUROPEAN JOURNAL OF ORGANIC CHEMISTRY(5),999-1006.
MLA	Li, Jia,et al."Asymmetric Synthesis of Aromatic and Heteroaromatic -Amino Acids Using a Recyclable Axially Chiral Ligand".EUROPEAN JOURNAL OF ORGANIC CHEMISTRY .5(2016):999-1006.