Asymmetric Transfer Hydrogenation of Trifluoromethylated Imines to Chiral α-Trifluoromethylated Amines With Alcohol as The Hydrogen Source

被引:3
作者
Wang, Zheting [1 ]
Yang, Chunhui [1 ]
Chen, Jingchao [1 ]
Yang, Fan [1 ]
Khan, Ruhima [1 ]
Yang, Yong [2 ]
Qiao, Xingfang [2 ]
Su, Zhimin [2 ]
Fan, Baomin [1 ,2 ]
机构
[1] Yunnan Minzu Univ, Key Lab Chem Ethn Med Resources, Yuehua St, Kunming 650500, Yunnan, Peoples R China
[2] Chongqing Acad Chinese Mat Med, Chongqing Key Lab Tradit Chinese Med Hlth, Chongqing, Peoples R China
基金
中国国家自然科学基金;
关键词
Asymmetric transfer hydrogenation; α -Trifluoromethylated imines; Chiral α -trifluoromethylated amines; Alcohols; Deuteration; PARTIALLY-MODIFIED RETRO; CATALYTIC ENANTIOSELECTIVE SYNTHESIS; ACID; REDUCTION; FLUORINE; ARYL; STRATEGIES; INHIBITOR; CHEMISTRY; DISCOVERY;
D O I
10.1002/ajoc.202100201
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient Pd/Zn co-catalyzed method for the asymmetric transfer hydrogenation of trifluoromethylated imines to chiral alpha-trifluoromethylated amines using methanol as the hydrogen source has been developed. The reaction showed good substrate scope and the products were obtained in excellent yields (up to 99%) with excellent enantioselectivity. The present methodology was compatible for the synthesis of deuterated chiral alpha-trifluoromethylated amines. On using CD3OD as the deuterium source, deuterium incorporation up to 98% was observed without compromising the reaction outcome.
引用
收藏
页码:1530 / 1535
页数:6
相关论文
共 67 条
[61]   Transition Metal-Catalyzed Enantioselective Hydrogenation of Enamines and Imines [J].
Xie, Jian-Hua ;
Zhu, Shou-Fei ;
Zhou, Qi-Lin .
CHEMICAL REVIEWS, 2011, 111 (03) :1713-1760
[62]   Asymmetric transfer hydrogenation reactions of N-sulfonylimines by using alcohols as hydrogen sources [J].
Yang, Fan ;
Chen, Jingchao ;
Shen, Guoli ;
Zhang, Xuexin ;
Fan, Baomin .
CHEMICAL COMMUNICATIONS, 2018, 54 (39) :4963-4966
[63]   Palladium/Lewis Acid Co-catalyzed Divergent Asymmetric Ring-Opening Reactions of Azabenzonorbornadienes with Alcohols [J].
Yang, Fan ;
Chen, Jingchao ;
Xu, Jianbin ;
Ma, Fujie ;
Zhou, Yongyun ;
Shinde, Madhuri Vikas ;
Fan, Baomin .
ORGANIC LETTERS, 2016, 18 (19) :4832-4835
[64]   Palladium/Lewis Acid Cocatalyzed Reductive Asymmetric Ring-Opening Reaction of Azabenzonorbornadienes with Tertiary Amines as the Hydrogen Source [J].
Zhang, Dapeng ;
Khan, Ruhima ;
Yang, Fan ;
Zhang, Xuexin ;
Shen, Guoli ;
Gao, Yang ;
Fan, Ruifeng ;
Sun, Weiqing ;
Fan, Baomin .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (26) :3464-3470
[65]   Amphiphilic Hyperbranched Polyethoxysiloxane: A Self-Templating Assembled Platform to Fabricate Functionalized Mesostructured Silicas for Aqueous Enantioselective Reactions [J].
Zhang, Kun ;
An, Juzeng ;
Su, Yanchao ;
Zhang, Jueyu ;
Wang, Ziyun ;
Cheng, Tanyu ;
Liu, Guohua .
ACS CATALYSIS, 2016, 6 (09) :6229-6235
[66]   Synthesis and SAR of [1,2,4]Triazolo[1,5-a]pyrimidines, a class of anticancer agents with a unique mechanism of tubulin inhibition [J].
Zhang, Nan ;
Ayral-Kaloustian, Semiramis ;
Nguyen, Thai ;
Afragola, Jay ;
Hernandez, Richard ;
Lucas, Judy ;
Gibbons, James ;
Beyer, Carl .
JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (02) :319-327
[67]   Rhodium-catalyzed transfer hydrogenation of quinoxalines with water as a hydrogen source [J].
Zhang, Xia ;
Chen, Jingchao ;
Khan, Ruhima ;
Shen, Guoli ;
He, Zhenxiu ;
Zhou, Yongyun ;
Fan, Baomin .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (48) :10142-10147