Synthesis of gem-disubstituted taurines by the regioselective ring-opening of 2,2-disubstituted aziridines with sodium bisulfite and sulfite
文献类型：期刊论文
| 作者 | Chen, Ning1; Zhu, Min2; Zhang, Wei2; Du, Da-Ming2; Xu, Jiaxi1 |
| 刊名 | AMINO ACIDS
 |
| 出版日期 | 2009-07-01 |
| 卷号 | 37期号:2页码:309-313 |
| 关键词 | Amino Acid Aminoalkanesulfonic Acid Ring-opening Reaction Sodium Bisulfite Sodium Sulfute Synthesis Taurine |
| ISSN号 | 0939-4451 |
| DOI | 10.1007/s00726-008-0153-3 |
| 英文摘要 | The regioselectivity of the ring-opening reactions of 2,2-disubstituted aziridines with sodium bisulfite and sulfite showed significant divergence depending on the nucleophiles and the structure of the substituents of the aziridines. 2,2-Dialkylaziridines were specifically attacked on their less substituted carbon atoms with sodium bisulfite, affording 2,2-substituted taurines, while 2,2-disubstituted aziridines with either one or two aryl substituent(s) were attacked specifically on their more substituted carbon atoms with the same nucleophile, giving rise to aromatic 1,1-substituted taurines. Sodium sulfite attacked the less substituted carbon atoms of all aziridines specifically to afford 2,2-disubstituted taurines. The regioselectivity is governed by the nucleophile and the balance between the steric hindrance and the electronic effect. The current method provides an alternative route to the synthesis of 2,2-dialkyltaurines and aromatic gem-disubstituted taurines. |
| 语种 | 英语 |
| WOS记录号 | WOS:000267679600011 |
| 出版者 | SPRINGER |
| 源URL | [http://ir.iccas.ac.cn/handle/121111/67857]  |
| 专题 | 中国科学院化学研究所 |
| 通讯作者 | Xu, Jiaxi |
| 作者单位 | 1.Beijing Univ Chem Technol, Fac Sci, Beijing 100029, Peoples R China 2.Peking Univ, Coll Chem & Mol Engn, BNLMS, Beijing 100871, Peoples R China |
| 推荐引用方式 GB/T 7714 | Chen, Ning,Zhu, Min,Zhang, Wei,et al. Synthesis of gem-disubstituted taurines by the regioselective ring-opening of 2,2-disubstituted aziridines with sodium bisulfite and sulfite[J]. AMINO ACIDS,2009,37(2):309-313. |
| APA | Chen, Ning,Zhu, Min,Zhang, Wei,Du, Da-Ming,&Xu, Jiaxi.(2009).Synthesis of gem-disubstituted taurines by the regioselective ring-opening of 2,2-disubstituted aziridines with sodium bisulfite and sulfite.AMINO ACIDS,37(2),309-313. |
| MLA | Chen, Ning,et al."Synthesis of gem-disubstituted taurines by the regioselective ring-opening of 2,2-disubstituted aziridines with sodium bisulfite and sulfite".AMINO ACIDS 37.2(2009):309-313. |
入库方式： OAI收割
来源：化学研究所
浏览0
下载0
收藏0
其他版本
除非特别说明，本系统中所有内容都受版权保护，并保留所有权利。