Chemical Dynamic Kinetic Resolution and S/R Interconversion of Unprotected alpha-Amino Acids
文献类型：期刊论文
| 作者 | Takeda, Ryosuke2; Kawamura, Akie2; Kawashima, Aki2; Sato, Tatsunori2; Moriwaki, Hiroki2; Izawa, Kunisuke2; Akaji, Kenichi3; Wang, Shuni1; Liu, Hong1 ; Luis Acena, Jose4
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| 刊名 | ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
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| 出版日期 | 2014-11-03 |
| 卷号 | 53期号:45页码:12214-12217 |
| 关键词 | amino acids chirality diastereoselectivity kinetic resolution nickel |
| ISSN号 | 1433-7851 |
| DOI | 10.1002/anie.201407944 |
| 文献子类 | Article |
| 英文摘要 | Reported herein is the first purely chemical method for the dynamic kinetic resolution (DKR) of unprotected racemic alpha-amino acids (alpha-AAs), a method which can rival the economic efficiency of the enzymatic reactions. The DKR reaction principle can be readily applied for S/R interconversions of alpha-AAs, the methodological versatility of which is unmatched by biocatalytic approaches. The presented process features a virtually complete stereochemical outcome, fully recyclable source of chirality, and operationally simple and convenient reaction conditions, thus allowing its ready scalability. A quite unique and novel mode of the thermodynamic control over the stereochemical outcome, including an exciting interplay between axial, helical, and central elements of chirality is proposed. |
| WOS关键词 | NUCLEOPHILIC GLYCINE EQUIVALENTS ; ENANTIOSELECTIVE BIOMIMETIC TRANSAMINATION ; OPERATIONALLY CONVENIENT CONDITIONS ; MICHAEL ADDITION-REACTIONS ; ASYMMETRIC-SYNTHESIS ; NI(II) COMPLEXES ; DIRECTED EVOLUTION ; SCHIFF-BASES ; (R)-3-AMINO-4,4,4-TRIFLUOROBUTANOIC ACID ; R INTERCONVERSION |
| 资助项目 | Ikerbasque[00000000] ; Basque Foundation for Science[00000000] ; Basque Government[SAIOTEK S-PE13UN098] ; National Natural Science Foundation of China[81025017] ; Hamari Chemicals (Osaka (Japan))[00000000] |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:000344052000039 |
| 出版者 | WILEY-V C H VERLAG GMBH |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/276844]  |
| 专题 | 药物化学研究室 |
| 通讯作者 | Moriwaki, Hiroki |
| 作者单位 | 1.Chinese Acad Sci, Shanghai Inst Mat Med, Key Lab Receptor Res, Shanghai 201203, Peoples R China; 2.Hamari Chem Ltd, Higashi Yodogawa Ku, Osaka 5330024, Japan; 3.Kyoto Pharmaceut Univ, Dept Med Chem, Kyoto 6078412, Japan; 4.Univ Basque Country UPV EHU, Fac Chem, Dept Organ Chem 1, San Sebastian 20018, Spain; 5.Basque Fdn Sci, Ikerbasque, Bilbao 48013, Spain |
| 推荐引用方式 GB/T 7714 | Takeda, Ryosuke,Kawamura, Akie,Kawashima, Aki,et al. Chemical Dynamic Kinetic Resolution and S/R Interconversion of Unprotected alpha-Amino Acids[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2014,53(45):12214-12217. |
| APA | Takeda, Ryosuke.,Kawamura, Akie.,Kawashima, Aki.,Sato, Tatsunori.,Moriwaki, Hiroki.,...&Soloshonok, Vadim A..(2014).Chemical Dynamic Kinetic Resolution and S/R Interconversion of Unprotected alpha-Amino Acids.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,53(45),12214-12217. |
| MLA | Takeda, Ryosuke,et al."Chemical Dynamic Kinetic Resolution and S/R Interconversion of Unprotected alpha-Amino Acids".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 53.45(2014):12214-12217. |
入库方式： OAI收割
来源：上海药物研究所
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