Effective asymmetric Michael addition of acetone to nitroalkenes promoted by chiral proline amide-thiourea bifunctional catalysts

被引：21
作者：
Wang, Qiao-wei [1 ,2 ]
Peng, Lin [1 ,2 ]
Fu, Ji-ya [1 ,2 ]
Huang, Qing-chun
Wang, Li-xin [1 ]
Xu, Xiao-ying [1 ]
机构：
[1] Chinese Acad Sci, Key Lab Asymmetr Synth & Chirotechnol Sichuan Pro, Chengdu Inst Organ Chem, Chengdu 610041, Peoples R China
[2] Chinese Acad Sci, Grad Sch, Beijing 100039, Peoples R China
来源：
ARKIVOC | 2010年
基金：
中国国家自然科学基金;
关键词：
Organocatalyst; Michael addition; acetone; trans-nitroalkenes; chiral proline amidethiourea; ENANTIOSELECTIVE CONJUGATE ADDITION; EFFICIENT ORGANOCATALYSTS; 1,4-ADDITION REACTIONS; PYRROLIDINE-THIOUREA; KETONES; ALDEHYDES; AMINE; NITROOLEFINS; DERIVATIVES; STEREOCENTERS;
D O I：
10.3998/ark.5550190.0011.229
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A series of secondary amine-thiourea catalysts 1a-1d derived from L-proline and chiral diamine were prepared and successfully applied to the Michael addition of acetone to trans-nitroalkenes in excellent yields (up to 99%) and enantioselectivities (44-91% ee).
引用
收藏
页码：340 / 351
页数：12
相关论文
共 50 条
[41]   Chiral Bifunctional Thiourea-Catalyzed Enantioselective Michael Addition of Ketones to Nitrodienes [J].
Ma, Hai ;
Liu, Kun ;
Zhang, Fa-Guang ;
Zhu, Chuan-Le ;
Nie, Jing ;
Ma, Jun-An .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (05) :1402-1409
[42]   Asymmetric Michael Addition of α-Substituted Isocyanoacetates with Maleimides Catalyzed by Chiral Tertiary Amine Thiourea [J].
Bai, Jian-Fei ;
Wang, Liang-Liang ;
Peng, Lin ;
Guo, Yun-Long ;
Jia, Li-Na ;
Tian, Fang ;
He, Guang-Yun ;
Xu, Xiao-Ying ;
Wang, Li-Xin .
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (06) :2947-2953
[43]   The first catalytic asymmetric addition of diethylzinc to aldehyde promoted by chiral thiourea [J].
Qiao, Zhi Guo ;
Shen, Tian Hua ;
Fu, Zhen Fang ;
Li, Jun Qi ;
Wang, Hong ;
Song, Qing Bao .
CHINESE CHEMICAL LETTERS, 2011, 22 (11) :1265-1268
[44]   A highly efficient large-scale asymmetric Michael addition of isobutyraldehyde to maleimides promoted by a novel multifunctional thiourea [J].
Ma, Zhi-wei ;
Liu, Yu-xia ;
Li, Pan-li ;
Ren, Hang ;
Zhu, Yu ;
Tao, Jing-chao .
TETRAHEDRON-ASYMMETRY, 2011, 22 (18-19) :1740-1748
[45]   Highly efficient asymmetric Michael addition of aldehydes to nitroalkenes with 4,5-methano-L-proline as organocatalysts [J].
Yu, Han ;
Liu, Mouming ;
Han, Sheng .
TETRAHEDRON, 2014, 70 (44) :8380-8384
[46]   Highly Enantioselective Michael Addition Promoted by a New Diterpene-Derived Bifunctional Thiourea Catalyst: A Doubly Stereocontrolled Approach to Chiral Succinimide Derivatives [J].
Song, Zhong-Tai ;
Zhang, Tao ;
Du, Hai-Long ;
Ma, Zhi-Wei ;
Zhang, Chang-Hua ;
Tao, Jing-Chao .
CHIRALITY, 2014, 26 (02) :121-127
[47]   Enantioselective Michael Addition of Nitroalkanes to Nitroalkenes Catalyzed by Chiral Bifunctional Quinine-Based Squaramides [J].
Kanberoglu, Esra ;
Tanyeli, Cihangir .
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 5 (01) :114-119
[48]   Double Diastereocontrol in Bifunctional Thiourea Organocatalysis: Iterative Michael-Michael-Henry Sequence Regulated by the Configuration of Chiral Catalysts [J].
Varga, Szilard ;
Jakab, Gergely ;
Drahos, Laszlo ;
Holczbauer, Tames ;
Czugler, Matyas ;
Soos, Tibor .
ORGANIC LETTERS, 2011, 13 (20) :5416-5419
[49]   Enantioselective Michael addition of nitroolefins and cyclohexanones catalyzed by novel pyrrolidine-thiourea bifunctional catalysts with two chiral centers [J].
Cheng, Dongping ;
Bao, Weiliang .
LETTERS IN ORGANIC CHEMISTRY, 2008, 5 (05) :342-345
[50]   An effective bifunctional thiourea catalyst for highly enantio- and diastereoselective Michael addition of cyclohexanone to nitroolefins [J].
Cao, Yi-Ju ;
Lu, Hai-Hua ;
Lai, Yuan-Yuan ;
Lu, Liang-Qiu ;
Xiao, Wen-Jing .
SYNTHESIS-STUTTGART, 2006, (22) :3795-3800
12345