Organocatalytic Asymmetric Reduction of Fluorinated Alkynyl Ketimines

被引：29
作者：
Chen, Mu-Wang [1 ,2 ]
Yang, Qin [1 ,2 ,3 ]
Deng, Zhihong [1 ,2 ]
Zhou, Yirong [1 ,2 ]
Ding, Quping [1 ,2 ,3 ]
Peng, Yiyuan [1 ,2 ,3 ]
机构：
[1] Jiangxi Normal Univ, Minist Educ, Key Lab Small Funct Organ Mol, Nanchang 330022, Jiangxi, Peoples R China
[2] Jiangxi Normal Univ, Coll Chem, Nanchang 330022, Jiangxi, Peoples R China
[3] Jiangxi Normal Univ, Jiangxis Key Lab Green Chem, Nanchang 330022, Jiangxi, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 15期
基金：
中国国家自然科学基金;
关键词：
CHIRAL PHOSPHORIC-ACID; CATALYZED TRANSFER HYDROGENATION; BRONSTED ACID; TRIFLUOROMETHYLATED AMINES; ENANTIOSELECTIVE SYNTHESIS; EFFICIENT SYNTHESIS; KINETIC RESOLUTION; DIRECT ACCESS; IMINES; BENZOTHIAZOLINE;
D O I：
10.1021/acs.joc.8b00873
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Highly chemoselective catalytic transfer hydrogenation of fluorinated alkynyl ketimines has been achieved by employing chiral phosphoric acid as a catalyst with benzothiazoline as a hydride source, providing the corresponding chiral fluorinated propargylamines in good yields and excellent enantioselectivities. In addition, iodocyclization of fluorinated propargylamine affords chiral 3-iodo-2-(trifluoromethyl)-1,2-dihydroquinoline, which can be easily converted to 2-(trifluoromethyl)- 1,2-dihydroquinoline derivatives with the selective COX -2 inhibitory activity.
引用
收藏
页码：8688 / 8694
页数：7
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