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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 PublicationJ. Am. Chem. Soc.
Volume137Issue:14Pages:4626-4629
AbstractThis 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
DOI10.1021/jacs.5b01517
URL查看原文
Indexed BySCI
Language英语
WOS IDWOS:000353177100009
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Document Type期刊论文
Identifierhttp://ir.sioc.ac.cn/handle/331003/39600
Collection金属有机化学国家重点实验室
Corresponding AuthorTang Y(唐勇)
Affiliation1.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.
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