Asymmetric 1,2-Perfluoroalkyl Migration: Easy Access to Enantioenriched alpha-Hydroxy-alpha-perfluoroalkyl Esters
文献类型：期刊论文
| 作者 | Wang P(王盼)1; Feng LW(冯良文)1; Wang LJ(王丽佳)1; Li JF(李军方)1; Liao SH(廖赛虎)1; Tang Y(唐勇)1 |
| 刊名 | J. Am. Chem. Soc.
 |
| 出版日期 | 2015 |
| 卷号 | 137期号:14页码:4626-4629 |
| 其他题名 | 不对称1,2-全氟烷基迁移: 对映选择性合成α-羟基α-全氟烷基酯 |
| 通讯作者 | 唐勇 |
| 英文摘要 | This study has led to the development of a novel, highly efficient, 1,2-perfluoro-alkyl/-aryl migration process in reactions of hydrate of 1-perfluoro-alkyl/-aryl-1,2-diketones with alcohols, which are promoted by a Zn(II)/bisoxazoline and form alpha-perfluoro-alkyl/-aryl-substituted a-hydroxy esters. With (-)-8-phenylmenthol as the alcohol, the corresponding menthol esters are generated in high yields with excellent levels of diastereoselectivity. The mechanistic studies show that the benzilic ester-type rearrangement reaction takes place via an unusual 1,2-migration of electron-deficient trifluoromethyl group rather than the phenyl group. The overall process serves as a novel, efficient, and simple approach for the synthesis of highly enantioenriched, biologically relevant alpha-hydroxy-alpha-perfluoroalkyl carboxylic acid derivatives. |
| 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/jacs.5b01517 |
| 语种 | 英语 |
| WOS记录号 | WOS:000353177100009 |
| 源URL | [http://ir.sioc.ac.cn/handle/331003/39600]  |
| 专题 | 上海有机化学研究所_金属有机化学国家重点实验室 |
| 作者单位 | 1.中科院上海有机化学研究所, 金属有机化学国家重点实验室 2.天津化学化工协同创新中心 |
| 推荐引用方式 GB/T 7714 | Wang P,Feng LW,Wang LJ,et al. Asymmetric 1,2-Perfluoroalkyl Migration: Easy Access to Enantioenriched alpha-Hydroxy-alpha-perfluoroalkyl Esters[J]. J. Am. Chem. Soc.,2015,137(14):4626-4629. |
| APA | 王盼,冯良文,王丽佳,李军方,廖赛虎,&唐勇.(2015).Asymmetric 1,2-Perfluoroalkyl Migration: Easy Access to Enantioenriched alpha-Hydroxy-alpha-perfluoroalkyl Esters.J. Am. Chem. Soc.,137(14),4626-4629. |
| MLA | 王盼,et al."Asymmetric 1,2-Perfluoroalkyl Migration: Easy Access to Enantioenriched alpha-Hydroxy-alpha-perfluoroalkyl Esters".J. Am. Chem. Soc. 137.14(2015):4626-4629. |
入库方式： OAI收割
来源：上海有机化学研究所
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