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学科主题: 金属有机化学
题名: Asymmetric 1,2-Perfluoroalkyl Migration: Easy Access to Enantioenriched alpha-Hydroxy-alpha-perfluoroalkyl Esters
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
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
通讯作者: 唐勇
刊名: J. Am. Chem. Soc.
发表日期: 2015
DOI: 10.1021/jacs.5b01517
卷: 137, 期:14, 页:4626-4629
收录类别: SCI
文章类型: 论文
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.
语种: 英语
相关网址: 查看原文
WOS记录号: WOS:000353177100009
Citation statistics:
内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/39600
Appears in Collections:金属有机化学国家重点实验室_期刊论文

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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

Recommended Citation:
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.
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