Synthesis of bis-alpha,alpha '-amino acids through diastereoselective bis-alkylations of chiral Ni(II)-complexes of glycine
文献类型：期刊论文
| 作者 | Wang, Jiang1 ; Liu, Hong1; Luis Acena, Jose2; Houck, Daniel2,3; Takeda, Ryosuke4; Moriwaki, Hiroki4; Sato, Tatsunori4; Soloshonok, Vadim A.2,3
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| 刊名 | ORGANIC & BIOMOLECULAR CHEMISTRY
 |
| 出版日期 | 2013-07-21 |
| 卷号 | 11期号:27页码:4508-4515 |
| ISSN号 | 1477-0520 |
| DOI | 10.1039/c3ob40594j |
| 文献子类 | Article |
| 英文摘要 | The Ni(II) complex derived from glycine Schiff base with (S)-N-(benzylprolyl)-2-aminobenzophenone can be effectively alkylated with alpha,omega-dibromide reagents to furnish the corresponding bis-alkylated products. This method presents a direct approach for the preparation of the corresponding bis-alpha,alpha'-amino acids with high biological importance. Heterogeneous (phase-transfer) as well as homogeneous conditions for the alkylation reactions have been investigated and the latter proved to be more efficient in terms of stereochemical outcome. In particular, alkylation of the glycine Schiff base Ni(II) complex with 1,3-dibromopropane followed by acid-catalysed hydrolysis of the resulting bis-alkylation product, allowed for the preparation of naturally occurring (2S,6S)-diaminopimelic acid in high overall yield. |
| WOS关键词 | ALPHA-AMINO-ACIDS ; MICHAEL ADDITION-REACTIONS ; ASYMMETRIC ALDOL REACTIONS ; PHASE-TRANSFER CATALYSIS ; NICKEL(II) SCHIFF-BASE ; PROTECTED MESO-2,6-DIAMINOPIMELIC ACID ; OPERATIONALLY CONVENIENT CONDITIONS ; SUBSTITUTED PYROGLUTAMIC ACIDS ; PURE 4-AMINOGLUTAMIC ACIDS ; VIRTUALLY COMPLETE CONTROL |
| 资助项目 | Ikerbasque[00000000] ; Basque Foundation for Science[00000000] ; National Natural Science Foundation of China[81025017] ; Basque Government[SAIOTEK S-PE12UN044] ; Hamari Chemicals (Osaka, Japan)[00000000] |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:000321601000012 |
| 出版者 | ROYAL SOC CHEMISTRY |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/277536]  |
| 专题 | 药物化学研究室 中科院受体结构与功能重点实验室 新药研究国家重点实验室 |
| 通讯作者 | Liu, Hong |
| 作者单位 | 1.Chinese Acad Sci, Shanghai Inst Biol Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China; 2.Univ Basque Country UPV EHU, Fac Chem, Dept Organ Chem 1, San Sebastian 20018, Spain; 3.Basque Fdn Sci, IKERBASQUE, Bilbao 48011, Spain; 4.Hamari Chem Ltd, Higashi Yodogawa Ku, Osaka 5330024, Japan |
| 推荐引用方式 GB/T 7714 | Wang, Jiang,Liu, Hong,Luis Acena, Jose,et al. Synthesis of bis-alpha,alpha '-amino acids through diastereoselective bis-alkylations of chiral Ni(II)-complexes of glycine[J]. ORGANIC & BIOMOLECULAR CHEMISTRY,2013,11(27):4508-4515. |
| APA | Wang, Jiang.,Liu, Hong.,Luis Acena, Jose.,Houck, Daniel.,Takeda, Ryosuke.,...&Soloshonok, Vadim A..(2013).Synthesis of bis-alpha,alpha '-amino acids through diastereoselective bis-alkylations of chiral Ni(II)-complexes of glycine.ORGANIC & BIOMOLECULAR CHEMISTRY,11(27),4508-4515. |
| MLA | Wang, Jiang,et al."Synthesis of bis-alpha,alpha '-amino acids through diastereoselective bis-alkylations of chiral Ni(II)-complexes of glycine".ORGANIC & BIOMOLECULAR CHEMISTRY 11.27(2013):4508-4515. |
入库方式： OAI收割
来源：上海药物研究所
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