Neighboring group participation of phosphine oxide functionality in the highly regio- and stereoselective iodohydroxylation of 1,2-allenylic diphenyl phosphine oxides
文献类型：期刊论文
| 作者 | Guo H(郭浩) ; Qian R(钱荣) ; Guo YL(郭寅龙) ; Ma SM(麻生明) |
| 刊名 | J. Org. Chem.
 |
| 出版日期 | 2008 |
| 卷号 | 73期号:20页码:7934-7938 |
| ISSN号 | 0022-3263 |
| 其他题名 | Neighboring group participation of phosphine oxide functionality in the highly regio- and stereoselective iodohydroxylation of 1,2-allenylic diphenyl phosphine oxides |
| 通讯作者 | 麻生明 |
| 英文摘要 | Two sets of reaction conditions were established to enable the highly regio- and stereoselective iodohydroxylation of 1,2-allenylic diphenyl phosphine oxides, yielding (E)-2-iodo-3-hydroxy-1-alkenyl diphenyl phosphine oxides with very high stereoselectivity. The scope of this reaction was examined extensively. Notably, studies on the reactivity of optically active substrates indicated that the axial. chirality in the starting allenes may be efficiently transferred to the center chirality of the products with no discernible loss of enantiopurity. Due to the importance of phosphine-containing compounds, both as reagents and ligands, this reaction shows potentials in organic synthesis. Investigations using ESI-MS technology on the O-18-labeled product, which was prepared using O-18-water as the solvent, indicated that the O-18 atom was bound to phosphorus in the final product and the oxygen atom of the hydroxyl comes from the phosphinyl functionality of the allene reactant. These results provided solid evidence for the formation of a five-membered cyclic intermediate from the neighboring group participation of the diphenylphosphinyl group. To the best of our knowledge, this is the first time that the neighboring group participation of this type of group was observed. |
| 学科主题 | 有机化学 |
| 收录类别 | SCI |
| 原文出处 | http://dx.doi.org/10.1021/jo8013462 |
| 语种 | 英语 |
| WOS记录号 | WOS:000259973900012 |
| 公开日期 | 2013-01-16 |
| 源URL | [http://202.127.28.38/handle/331003/12152]  |
| 专题 | 上海有机化学研究所_金属有机化学国家重点实验室 |
| 推荐引用方式 GB/T 7714 | Guo H,Qian R,Guo YL,et al. Neighboring group participation of phosphine oxide functionality in the highly regio- and stereoselective iodohydroxylation of 1,2-allenylic diphenyl phosphine oxides[J]. J. Org. Chem.,2008,73(20):7934-7938. |
| APA | 郭浩,钱荣,郭寅龙,&麻生明.(2008).Neighboring group participation of phosphine oxide functionality in the highly regio- and stereoselective iodohydroxylation of 1,2-allenylic diphenyl phosphine oxides.J. Org. Chem.,73(20),7934-7938. |
| MLA | 郭浩,et al."Neighboring group participation of phosphine oxide functionality in the highly regio- and stereoselective iodohydroxylation of 1,2-allenylic diphenyl phosphine oxides".J. Org. Chem. 73.20(2008):7934-7938. |
入库方式： OAI收割
来源：上海有机化学研究所
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