| Asymmetric 1,2-Perfluoroalkyl Migration: Easy Access to Enantioenriched alpha-Hydroxy-alpha-perfluoroalkyl Esters | |
| Alternative Title | 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 |
| 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 | |
| 2015 | |
| Source Publication | J. Am. Chem. Soc.
 |
| Volume | 137Issue:14Pages:4626-4629 |
| Abstract | 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. |
| Subtype | 论文 |
| Subject Area | 金属有机化学 |
| DOI | 10.1021/jacs.5b01517 |
| URL | 查看原文 |
| Indexed By | SCI |
| Language | 英语 |
| WOS ID | WOS:000353177100009 |
| Citation statistics | |
| Document Type | 期刊论文 |
| Identifier | http://ir.sioc.ac.cn/handle/331003/39600 |
| Collection | 金属有机化学国家重点实验室 |
| Corresponding Author | Tang Y(唐勇) |
| Affiliation | 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 |
| Recommended Citation 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. |
| Files in This Item: | ||||||
| File Name/Size | DocType | Version | Access | License | ||
| 2015243.pdf（659KB） | 期刊论文 | 作者接受稿 | 开放获取 | CC BY-NC-SA | Application Full Text | |
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