Assignment of absolute configuration of cyclic secondary amines by NMR techniques using Mosher's method: a general procedure exemplified with (-)-isoanabasine
文献类型：期刊论文
| 作者 | Kang, CQ; Guo, HQ; Qiu, XP; Bai, XL; Yao, HB; Gao, LX |
| 刊名 | MAGNETIC RESONANCE IN CHEMISTRY
 |
| 出版日期 | 2006 |
| 卷号 | 44期号:1页码:20-24 |
| 关键词 | H-1 Nmr C-13 Nmr Absolute Configuration Mosher's Method Isoanabasine Cyclic Secondary Amine Enantiomeric Excess |
| ISSN号 | 0749-1581 |
| DOI | 10.1002/mrc.1716 |
| 英文摘要 | A general procedure to determine the absolute configuration of cyclic secondary amines with Mosher's NMR method is demonstrated, with assignment of absolute configuration of isoanabasine as an example. Each Mosher amide can adopt two stable conformations (named rotamers) caused by hindered rotation around amide C-N bond. Via a three-step structural analysis of four rotamers, the absolute configuration of (-)-isoanabasine is deduced to be (R) on the basis of Newman projections, which makes it easy to understand and clarify the application of Mosher's method to cyclic secondary amines. Furthermore, it was observed that there was an unexpected ratio of rotamers of Mosher amide derived from (R)-isoanabasine and (R)-Mosher acid. This phenomenon implied that it is necessary to distinguish the predominant rotamer from the minor one prior to determining the absolute configuration while using this technique. Copyright (c) 2005 John Wiley & Sons, Ltd. |
| 语种 | 英语 |
| WOS记录号 | WOS:000234603900004 |
| 出版者 | JOHN WILEY & SONS LTD |
| 源URL | [http://ir.iccas.ac.cn/handle/121111/60273]  |
| 专题 | 中国科学院化学研究所 |
| 通讯作者 | Gao, LX |
| 作者单位 | Chinese Acad Sci, Changchun Inst Appl Chem, State Key Lab Polymer Phys & Chem, Changchun 130022, Peoples R China |
| 推荐引用方式 GB/T 7714 | Kang, CQ,Guo, HQ,Qiu, XP,et al. Assignment of absolute configuration of cyclic secondary amines by NMR techniques using Mosher's method: a general procedure exemplified with (-)-isoanabasine[J]. MAGNETIC RESONANCE IN CHEMISTRY,2006,44(1):20-24. |
| APA | Kang, CQ,Guo, HQ,Qiu, XP,Bai, XL,Yao, HB,&Gao, LX.(2006).Assignment of absolute configuration of cyclic secondary amines by NMR techniques using Mosher's method: a general procedure exemplified with (-)-isoanabasine.MAGNETIC RESONANCE IN CHEMISTRY,44(1),20-24. |
| MLA | Kang, CQ,et al."Assignment of absolute configuration of cyclic secondary amines by NMR techniques using Mosher's method: a general procedure exemplified with (-)-isoanabasine".MAGNETIC RESONANCE IN CHEMISTRY 44.1(2006):20-24. |
入库方式： OAI收割
来源：化学研究所
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