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

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 10卷 / 06期

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

页码：1530 / 1535

页数：6

共 50 条

[1] Asymmetric Synthesis of Trifluoromethylated Amines via Catalytic Enantioselective Isomerization of Imines
Wu, Yongwei
Deng, Li
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (35) : 14334 - 14337
[2] Asymmetric Synthesis of Trifluoromethylated Amines and Their Derivatives
Cheng, Gui-Lin
Wang, Hui
Lin, Xian-Fu
Wu, Qi
[J]. CURRENT ORGANIC SYNTHESIS, 2016, 13 (04) : 514 - 543
[3] Chiral Phosphoric Acid Catalyzed Transfer Hydrogenation: Facile Synthetic Access to Highly Optically Active Trifluoromethylated Amines
Henseler, Alexander
Kato, Masanori
Mori, Keiji
Akiyama, Takahiko
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (35) : 8180 - 8183
[4] Asymmetric syntheses of valuable chiral trifluoromethylated enamides
Weinzierl, David
Waser, Mario
[J]. CHEM CATALYSIS, 2023, 3 (12):
[5] Synthesis of ?,?-Chiral Trifluoromethylated Amines through the Stereospecific Isomerization of ?-Chiral Allylic Amines
Garcia-Vazquez, Victor
Martinez-Pardo, Pablo
Postole, Alexandru
Inge, A. Ken
Martin-Matute, Belen
[J]. ORGANIC LETTERS, 2022, 24 (21) : 3867 - 3871
[6] Asymmetric Transfer Hydrogenation of Stable NH Imines for the Synthesis of Enantiopure α-Chiral Primary Amines
Zhang, Mangang
Li, Hui
Wu, Keqin
Rong, Nianxin
Lin, Shaoquan
Yang, Hua
Yin, Qin
[J]. CHINESE JOURNAL OF CHEMISTRY, 2024, 42 (18) : 2211 - 2216
[7] Synthesis of chiral trifluoromethylated amines by palladium-catalyzed diastereoselective hydrogenation-hydrogenolysis approach
Török, B
Prakash, GKS
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (1-2) : 165 - 168
[8] Unprecedented enantioselective reduction of N-unsubstituted imines: Catalytic asymmetric synthesis of trifluoromethylated amines.
Gosselin, F
O'Shea, PD
Roy, S
Reamer, R
Chen, CY
Volante, RP
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 229 : U555 - U555
[9] Asymmetric synthesis of chiral trifluoromethylated heliotridane via highly catalytic asymmetric Friedel-Crafts alkylation with β-trifluoromethylated acrylates and pyrroles
Huang, Yiyong
Suzuki, Satoru
Liu, Guokai
Tokunaga, Etsuko
Shiro, Motoo
Shibata, Norio
[J]. NEW JOURNAL OF CHEMISTRY, 2011, 35 (11) : 2614 - 2621
[10] Asymmetric Transfer Hydrogenation of Imines using Alcohol: Efficiency and Selectivity are Influenced by the Hydrogen Donor
Pan, Hui-Jie
Zhang, Yao
Shan, Chunhui
Yu, Zhaoyuan
Lan, Yu
Zhao, Yu
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (33) : 9615 - 9619

← 1 2 3 4 5 →