Asymmetric Michael reactions of α,α-disubstituted aldehydes with maleimides using a primary amine thiourea organocatalyst

被引:42
作者
Miura, Tsuyoshi [1 ]
Masuda, Akira [1 ]
Ina, Mariko [1 ]
Nakashima, Kosuke [1 ]
Nishida, Shohei [1 ]
Tada, Norihiro [1 ]
Itoh, Akichika [1 ]
机构
[1] Gifu Pharmaceut Univ, Gifu 5011196, Japan
基金
日本学术振兴会;
关键词
ENANTIOSELECTIVE CONJUGATE ADDITION; ALDOL REACTIONS; GUANIDINE;
D O I
10.1016/j.tetasy.2011.09.006
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Primary amine thiourea organocatalyst 8 was used to promote Michael additions of bulky alpha,alpha-disubstituted aldehydes, such as isobutyraldehyde with maleimides to afford the corresponding adducts in high to excellent yields and with up to 91% ee. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1605 / 1609
页数:5
相关论文
共 27 条
[1]  
Ahmed S, 1996, Drug Des Discov, V14, P77
[2]   Enantioselective Organocatalytic Addition of Azlactones to Maleimides: A Highly Stereocontrolled Entry to 2,2-Disubstituted-2H-oxazol-5-ones [J].
Alba, Andrea-Nekane R. ;
Valero, Guillem ;
Calbet, Teresa ;
Font-Bardia, Merce ;
Moyano, Albert ;
Rios, Ramon .
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (32) :9884-9889
[3]   Chiral primary amine thiourea promoted highly enantioselective Michael reactions of isobutylaldehyde with maleimides [J].
Bai, Jian-Fei ;
Peng, Lin ;
Wang, Liang-liang ;
Wang, Li-Xin ;
Xu, Xiao-Ying .
TETRAHEDRON, 2010, 66 (46) :8928-8932
[4]   Conjugate addition of nitroalkanes to N-substituted maleimides.: Synthesis of 3-alkylsuccinimides and pyrrolidines [J].
Ballini, R ;
Bosica, G ;
Cioci, G ;
Fiorini, D ;
Petrini, M .
TETRAHEDRON, 2003, 59 (20) :3603-3608
[5]   Organocatalytic asymmetric conjugate addition of 1,3-dicarbonyl compounds to maleimides [J].
Bartoli, Giuseppe ;
Bosco, Marcella ;
Carlone, Armando ;
Cavalli, Andrea ;
Locatelli, Manuela ;
Mazzanti, Andrea ;
Ricci, Paolo ;
Sambri, Letizia ;
Melchiorre, Paolo .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (30) :4966-4970
[6]   Succinimide hydroxamic acids as potent inhibitors of histone deacetylase (HDAC) [J].
Curtin, ML ;
Garland, RB ;
Heyman, HR ;
Frey, RR ;
Michaelides, MR ;
Li, JL ;
Pease, LJ ;
Glaser, KB ;
Marcotte, PA ;
Davidsen, SK .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (20) :2919-2923
[7]  
HAMAD ASS, 2000, ELGAZWY MOL, V5, P665
[8]   Rate Acceleration of Triethylamine-Mediated Guanidine-Catalyzed Enantioselective Michael Reaction [J].
Jiang, Zhiyong ;
Ye, Weiping ;
Yang, Yuanyong ;
Tan, Choon-Hong .
ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (14-15) :2345-2351
[9]   Synthesis of a Chiral Quaternary Carbon Center Bearing a Fluorine Atom: Enantio- and Diastereoselective Guanidine-Catalyzed Addition of Fluorocarbon Nucleophiles [J].
Jiang, Zhiyong ;
Pan, Yuanhang ;
Zhao, Yujun ;
Ma, Ting ;
Lee, Richmond ;
Yang, Yuanyong ;
Huang, Kuo-Wei ;
Wong, Ming Wah ;
Tan, Choon-Hong .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (20) :3627-3631
[10]  
Katritzky AR, 1998, HETEROCYCLES, V48, P2677