Preference of 4-exo ring closure in copper-catalyzed intramolecular coupling of vinyl bromides with alcohols
文献类型：期刊论文
| 作者 | Fang YW(方烨汶) ; Li CZ(李超忠) |
| 刊名 | J. Am. Chem. Soc.
 |
| 出版日期 | 2007 |
| 卷号 | 129期号:26页码:8092-8093 |
| ISSN号 | 0002-7863 |
| 其他题名 | 铜催化下分子内烯基溴与醇偶联反应中4-exo环合的优先 |
| 通讯作者 | 李超忠 |
| 英文摘要 | The copper-catalyzed intramolecular O-vinylation of gamma-bromohomoallylic alcohols was investigated. With 10 mol % of CuI as the catalyst and 20 mol % of 1,10-phenanthroline as the ligand, the reactions of 3-bromo-3-buten-1-ols in refluxing CH3CN led to the convenient formation of the corresponding 2-methyleneoxetanes in good to excellent yields via a 4-exo ring closure. The configuration of the CC bond was nicely retained. This methodology was then successfully extended to the cyclization in 5-exo, 6-exo, and even 6-endo modes. Moreover, the competition experiments revealed that 4-exo cyclization is fundamentally preferred over other modes of cyclization. On the other hand, the corresponding Pd(0)-catalyzed O-vinylation showed the predominance of 5-exo over 4-exo cyclization. |
| 学科主题 | 金属有机化学 |
| 收录类别 | SCI |
| 原文出处 | http://dx.doi.org/10.1021/ja072793 |
| 语种 | 英语 |
| WOS记录号 | WOS:000247563700021 |
| 公开日期 | 2013-03-04 |
| 源URL | [http://202.127.28.38/handle/331003/22828]  |
| 专题 | 上海有机化学研究所_中科院天然产物有机化学重点实验室 |
| 推荐引用方式 GB/T 7714 | Fang YW,Li CZ. Preference of 4-exo ring closure in copper-catalyzed intramolecular coupling of vinyl bromides with alcohols[J]. J. Am. Chem. Soc.,2007,129(26):8092-8093. |
| APA | 方烨汶,&李超忠.(2007).Preference of 4-exo ring closure in copper-catalyzed intramolecular coupling of vinyl bromides with alcohols.J. Am. Chem. Soc.,129(26),8092-8093. |
| MLA | 方烨汶,et al."Preference of 4-exo ring closure in copper-catalyzed intramolecular coupling of vinyl bromides with alcohols".J. Am. Chem. Soc. 129.26(2007):8092-8093. |
入库方式： OAI收割
来源：上海有机化学研究所
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