Asymmetric Hydroaminoalkylation of Alkenylazaarenes via Cooperative Photoredox and Chiral Hydrogen-Bonding Catalysis

被引:58
作者
Chai, Xiangpei [1 ]
Hu, Xinheng [2 ]
Zhao, Xiaowei [2 ]
Yin, Yanli [1 ,3 ]
Cao, Shanshan [1 ]
Jiang, Zhiyong [1 ,2 ]
机构
[1] Henan Normal Univ, Sch Chem & Chem Engn, Xinxiang 453007, Henan, Peoples R China
[2] Henan Univ, Int S&T Cooperat Base Chiral Chem, Kaifeng 475004, Henan, Peoples R China
[3] Henan Univ Technol, Coll Bioengn, Zhengzhou 450001, Henan, Peoples R China
基金
中国国家自然科学基金; 中国博士后科学基金;
关键词
Asymmetric Photoredox Catalysis; Azaarenes; Conjugate Addition; Hydrogen-Bonding Catalysis; Nonclassical Interaction; ACID CATALYSIS;
D O I
10.1002/anie.202115110
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Chiral hydrogen-bonding (H-bonding) catalytic asymmetric conjugate addition to activated olefins has been widely used to access enantioenriched molecules containing stereocenters at the beta-position of the olefin activating groups. Herein, we report the first highly enantioselective radical-based manifold. Under a dual organocatalyst system involving a chiral phosphoric acid and DPZ as the photoredox sensitizer, transformations of N-arylglycines, in which aryls with CF3 substituents are introduced, with alkenyl azaarenes afforded valuable hydroaminoalkylation adducts with satisfactory results. In addition to the diversity of azaarenes, the method can be used to construct aryl-, alkyl- and silyl-substituted stereocenter. Control experiments and density functional theory calculations were performed to elucidate a plausible reaction mechanism and the origin of stereoselectivity, wherein nonclassical H-bonding interactions were found to assist chiral catalysts in offering sufficient enantiocontrol.
引用
收藏
页数:8
相关论文
共 51 条
[1]   Non-Classical C-H•••X Hydrogen Bonding and Its Role in Asymmetric Organocatalysis [J].
Ajitha, Manjaly J. ;
Huang, Kuo-Wei .
SYNTHESIS-STUTTGART, 2016, 48 (20) :3449-3458
[2]   Enantioselective Mannich-type reaction catalyzed by a chiral Bronsted acid [J].
Akiyama, T ;
Itoh, J ;
Yokota, K ;
Fuchibe, K .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (12) :1566-1568
[3]   Stronger bronsted acids [J].
Akiyama, Takahiko .
CHEMICAL REVIEWS, 2007, 107 (12) :5744-5758
[4]  
[Anonymous], 2004, Angew. Chem, V116, P1592
[5]  
[Anonymous], 2019, ANGEW CHEM, V131, P1600
[6]  
[Anonymous], 2013, ANGEW CHEM, V125, P6798
[7]  
[Anonymous], 2019, ANGEW CHEM, V131, P15950
[8]   Catalytic Enantioselective Addition of Prochiral Radicals to Vinylpyridines [J].
Cao, Kangning ;
Tan, Siu Min ;
Lee, Richmond ;
Yang, Songwei ;
Jia, Hongshao ;
Zhao, Xiaowei ;
Qiao, Baokun ;
Jiang, Zhiyong .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (13) :5437-5443
[9]   Enantioselective Synthesis of γ-Oxycarbonyl Motifs by Conjugate Addition of Photogenerated α-Alkoxy Radicals [J].
Dong, Xiao ;
Li, Qi Yukki ;
Yoon, Tehshik P. .
ORGANIC LETTERS, 2021, 23 (15) :5703-5708
[10]   Photocatalytic decarboxylative alkylations mediated by triphenylphosphine and sodium iodide [J].
Fu, Ming-Chen ;
Shang, Rui ;
Zhao, Bin ;
Wang, Bing ;
Fu, Yao .
SCIENCE, 2019, 363 (6434) :1429-+