Asymmetric Synthesis of Aromatic and Heteroaromatic -Amino Acids Using a Recyclable Axially Chiral Ligand
文献类型：期刊论文
| 作者 | Li, Jia1,2 ; Zhou, Shengbin2; Wang, Jiang2; Kawashima, Aki3; Moriwaki, Hiroki3; Soloshonok, Vadim A.3,4; Liu, Hong1,2
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| 刊名 | EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
 |
| 出版日期 | 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. |
| 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 |
| 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研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:000370337700020 |
| 出版者 | WILEY-V C H VERLAG GMBH |
| 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. |
入库方式： OAI收割
来源：上海药物研究所
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