Benzoylthiourea-Pyrrolidine as Another Bifunctional Organocatalyst: Highly Enantioselective Michael Addition of Cyclohexanone to Nitroolefins

被引：27
作者：
Ban, Shu-rong [1 ]
Zhu, Xi-xia [1 ]
Zhang, Zhi-ping [1 ]
Xie, Hong-yu [1 ]
Li, Qing-shan [1 ]
机构：
[1] Shanxi Med Univ, Sch Pharmaceut Sci, Taiyuan 030001, Peoples R China
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 2013卷 / 15期
基金：
中国国家自然科学基金;
关键词：
Organocatalysis; Diastereoselectivity; Enantioselectivity; Michael addition; Nitroalkenes; CHIRAL BRONSTED ACID; ASYMMETRIC CATALYSIS; ALPHA; BETA-UNSATURATED KETONES; PHOSPHONIUM SALTS; ALDOL REACTIONS; THIOUREA; MANNICH; PROLINE; ALDEHYDES; FLUORINATION;
D O I：
10.1002/ejoc.201300225
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Asymmetric Michael addition of cyclohexanone to nitrostyrenes in the presence of organocatalyst 1 (10 mol-%) and 2,4-dichlorobenzoic acid (10 mol-%) afforded the corresponding synthetically valuable gamma-nitroketones in moderate to good yields with high diastereoselectivities (up to >99:1 dr) and high enantioselectivities (up to >99% ee) under mild conditions.
引用
收藏
页码：2977 / 2980
页数：4
相关论文
共 96 条
[1]   Squaramides: Bridging from Molecular Recognition to Bifunctional Organocatalysis [J].
Aleman, Jose ;
Parra, Alejandro ;
Jiang, Hao ;
Jorgensen, Karl Anker .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (25) :6890-6899
[2]  
[Anonymous], 2004, Angew. Chem, V116, P5248, DOI DOI 10.1002/ANGE.200400650
[3]  
[Anonymous], 2008, ANGEW CHEM
[4]  
[Anonymous], 2009, ANGEW CHEM-GER EDIT
[5]   Highly asymmetric Michael additions of α,α-disubstituted aldehydes to β-nitroalkenes promoted by chiral pyrrolidine-thiourea bifunctional catalysts [J].
Bai, Jian-Fei ;
Xu, Xiao-Ying ;
Huang, Qing-Chun ;
Peng, Lin ;
Wang, Li-Xin .
TETRAHEDRON LETTERS, 2010, 51 (21) :2803-2805
[6]   Highly Enantioselective Michael Addition of Ketones to Nitroolefins with a Pyrrolidine-Based Phthalimide as an Enamine-Type Organocatalyst [J].
Ban, Shu-rong ;
Xie, Hong-yu ;
Zhu, Xi-xia ;
Li, Qing-shan .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (32) :6413-6417
[7]  
Ban SR, 2011, CHINESE J ORG CHEM, V31, P1350
[8]   Synthesis of Binaphthyl Sulfonimides and Their Application in the Enantioselective Michael Addition of Ketones to Nitroalkenes [J].
Ban, Shurong ;
Du, Da-Ming ;
Liu, Han ;
Yang, Wen .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (27) :5160-5164
[9]   Highly efficient dynamic kinetic resolution of azlactones by urea-based bifunctional organocatalysts [J].
Berkessel, A ;
Cleemann, F ;
Mukherjee, S ;
Müller, TN ;
Lex, J .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (05) :807-811
[10]  
Berkessel A., 2005, ANGEW CHEM, V117, P817
12345678910