期刊
JOURNAL OF FLUORINE CHEMISTRY
卷 128, 期 3, 页码 170-173出版社
ELSEVIER SCIENCE SA
DOI: 10.1016/j.jfluchem.2006.11.011
关键词
1,3-proton shift reaction; fluorine and compounds; imines; operationally convenient conditions; biomimetic reductive amination; cinchonidine derived bases; catalytic asymmetric synthesis
Here we describe catalytic asymmetric synthesis of alpha-(trifluoromethyl)benzylamine (1) via biomimetic transarnination using chiral base. Imine 4 was isomerized to Schiff base 5 using 50 mol.% of cinchonidine derivatives as a catalyst in chloroform, methanol or acetonitrile. In the case of cinchonidine 6 as a catalyst, the reaction conducted in chloroform allowed for 79% conversion of the starting imine 4 in 52 days. The product imine 5 was obtained of (R) absolute configuration in 35% ee as individual compound without any byproducts. The catalyst 6 can be recovered (> 95%) by adding n-hexane to the reaction mixture followed by a simple filtration. (c) 2006 Elsevier B.V. All rights reserved.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据