Highly Enantioselective Synthesis of Tetrahydroquinolines via Cobalt(II)-Catalyzed Tandem 1,5-Hydride Transfer/Cyclization

被引:133
作者
Cao, Weidi [1 ]
Liu, Xiaohua [1 ]
Wang, Wentao [1 ]
Lin, Lili [1 ]
Feng, Xiaoming [1 ]
机构
[1] Sichuan Univ, Coll Chem, Minist Educ, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China
基金
中国国家自然科学基金;
关键词
H BOND FUNCTIONALIZATION; FRIEDEL-CRAFTS ALKYLATION; DIELS-ALDER REACTION; ASYMMETRIC HYDROGENATION; EFFICIENT SYNTHESIS; MICHAEL ADDITION; REDOX PROCESS; QUINOLINES; COMPLEX; HETEROCYCLES;
D O I
10.1021/ol1028282
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A chiral catalyst prepared from N,N '-dioxide and Co(BF4)(2)center dot 6H(2)O was applied in the asymmetric hydride transfer initiated cyclization reaction, giving optically active tetrahydroquinolines in good yields with high enantioselectivities under mild reaction conditions. Meanwhile, in light of the absolute configuration of the product, a possible working model was proposed to explain the origin of the activation and asymmetric induction.
引用
收藏
页码:600 / 603
页数:4
相关论文
共 38 条
[1]  
Barton D., 1999, Comprehensive Natural Products Chemistry, V1
[2]   Organocatalytic asymmetric Povarov reactions with 2- and 3-vinylindoles [J].
Bergonzini, Giulia ;
Gramigna, Lucia ;
Mazzanti, Andrea ;
Fochi, Mariafrancesca ;
Bernardi, Luca ;
Ricci, Alfredo .
CHEMICAL COMMUNICATIONS, 2010, 46 (02) :327-329
[3]   Catalytic Asymmetric Bromoamination of Chalcones: Highly Efficient Synthesis of Chiral α-Bromo-β-Amino Ketone Derivatives [J].
Cai, Yunfei ;
Liu, Xiaohua ;
Hui, Yonghai ;
Jiang, Jun ;
Wang, Wentao ;
Chen, Weiliang ;
Lin, Lili ;
Feng, Xiaoming .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (35) :6160-6164
[4]   Highly Enantioselective Michael Addition of Malonate Derivatives to Enones Catalyzed by an N,N′-Dioxide-Scandium(III) Complex [J].
Chen, Donghui ;
Chen, Zhenling ;
Xiao, Xiao ;
Yang, Zhigang ;
Lin, Lili ;
Liu, Xiaohua ;
Feng, Xiaoming .
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (28) :6807-6810
[5]  
Glushkov V.A., 2008, RUSS CHEM REV+, V77, P137, DOI [10.1070/rc2008v077n02abeh003749, DOI 10.1070/RC2008V077N02ABEH003749, 10.1070/RC2008v077n02ABEH003749]
[6]   The development of double axially chiral phosphoric acids and their catalytic transfer hydrogenation of quinolines [J].
Guo, Qun-Sheng ;
Du, Da-Ming ;
Xu, Jiaxi .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (04) :759-762
[7]   Highly Enantioselective Conjugate Addition of Thioglycolate to Chalcones Catalyzed by Lanthanum: Low Catalyst Loading and Remarkable Chiral Amplification [J].
Hui, Yonghai ;
Jiang, Jun ;
Wang, Wentao ;
Chen, Weiliang ;
Cai, Yunfei ;
Lin, Lili ;
Liu, Xiaohua ;
Feng, Xiaoming .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (25) :4290-4293
[8]   Enantioselective Organocatalytic C-H Bond Functionalization via Tandem 1,5-Hydride Transfer/Ring Closure: Asymmetric Synthesis of Tetrahydroquinolines [J].
Kang, Young Ku ;
Kim, Sun Mi ;
Kim, Dae Young .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (34) :11847-11849
[9]   Recent progress in the synthesis of 1,2,3,4-tetrahydroquinolines [J].
Katritzky, AR ;
Rachwal, S ;
Rachwal, B .
TETRAHEDRON, 1996, 52 (48) :15031-15070
[10]  
kiyama T., 2006, J AM CHEM SOC, V128, P13070