Advanced asymmetric synthesis of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid by alkylation/cyclization of newly designed axially chiral Ni(II) complex of glycine Schiff base
文献类型：期刊论文
| 作者 | Kawashima, Aki2; Shu, Shuangjie3; Takeda, Ryosuke2; Kawamura, Akie2; Sato, Tatsunori2; Moriwaki, Hiroki2; Wang, Jiang3 ; Izawa, Kunisuke2; Luis Acena, Jose1; Soloshonok, Vadim A.1,4
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| 刊名 | AMINO ACIDS
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| 出版日期 | 2016-04 |
| 卷号 | 48期号:4页码:973-986 |
| 关键词 | Anti-viral (HCV) activity Asymmetric synthesis Amino acids Chirality Schiff bases |
| ISSN号 | 0939-4451 |
| DOI | 10.1007/s00726-015-2138-3 |
| 文献子类 | Article |
| 英文摘要 | Asymmetric synthesis of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid (vinyl-ACCA) is in extremely high demand due to the pharmaceutical importance of this tailor-made, sterically constrained alpha-amino acid. Here we report the development of an advanced procedure for preparation of the target amino acid via two-step S(N)2 and S(N)2' alkylation of novel axially chiral nucleophilic glycine equivalent. Excellent yields and diastereoselectivity coupled with reliable and easy scalability render this method of immediate use for practical synthesis of (1R,2S)-vinyl-ACCA. |
| WOS关键词 | ALPHA-AMINO-ACIDS ; OPERATIONALLY CONVENIENT CONDITIONS ; MICHAEL ADDITION-REACTIONS ; VIRUS NS3/4A PROTEASE ; SUBSTITUTED PYROGLUTAMIC ACIDS ; PURE 4-AMINOGLUTAMIC ACIDS ; VIRTUALLY COMPLETE CONTROL ; NUCLEOPHILIC GLYCINE ; STEREOSELECTIVE-SYNTHESIS ; EFFICIENT SYNTHESIS |
| 资助项目 | IKERBASQUE, Basque Foundation for Science[00000000] ; Basque Government[SAIOTEK S-PE13UN098] |
| WOS研究方向 | Biochemistry & Molecular Biology |
| 语种 | 英语 |
| WOS记录号 | WOS:000372551100007 |
| 出版者 | SPRINGER WIEN |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/276095]  |
| 专题 | 药物化学研究室 |
| 通讯作者 | Soloshonok, Vadim A. |
| 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.Hamari Chem Ltd, Higashi Yodogawa Ku, 1-4-29 Kunijima, Osaka 5330024, Japan; 3.Chinese Acad Sci, Shanghai Inst Mat Med, Key Lab Receptor Res, 555 Zu Chong Zhi Rd, Shanghai 201203, Peoples R China; 4.Ikerbasque, Basque Fdn Sci, Maria Diaz de Haro 3, Bilbao 48013, Spain |
| 推荐引用方式 GB/T 7714 | Kawashima, Aki,Shu, Shuangjie,Takeda, Ryosuke,et al. Advanced asymmetric synthesis of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid by alkylation/cyclization of newly designed axially chiral Ni(II) complex of glycine Schiff base[J]. AMINO ACIDS,2016,48(4):973-986. |
| APA | Kawashima, Aki.,Shu, Shuangjie.,Takeda, Ryosuke.,Kawamura, Akie.,Sato, Tatsunori.,...&Liu, Hong.(2016).Advanced asymmetric synthesis of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid by alkylation/cyclization of newly designed axially chiral Ni(II) complex of glycine Schiff base.AMINO ACIDS,48(4),973-986. |
| MLA | Kawashima, Aki,et al."Advanced asymmetric synthesis of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid by alkylation/cyclization of newly designed axially chiral Ni(II) complex of glycine Schiff base".AMINO ACIDS 48.4(2016):973-986. |
入库方式： OAI收割
来源：上海药物研究所
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