Organocatalytic Michael addition of unprotected 3-substituted oxindoles to nitroolefins

被引:70
作者
Ding, Miao [1 ]
Zhou, Feng [1 ]
Qian, Zi-Qing [1 ]
Zhou, Jian [1 ]
机构
[1] E China Normal Univ, Shanghai Key Lab Green Chem & Chem Proc, Dept Chem, Shanghai 200062, Peoples R China
关键词
FRIEDEL-CRAFTS ALKYLATION; CATALYTIC ASYMMETRIC-SYNTHESIS; QUATERNARY STEREOGENIC CENTERS; ENANTIOSELECTIVE SYNTHESIS; CONJUGATE ADDITION; CARBENE LIGANDS; ALPHA-ARYLATION; THIOUREA; NITROALKENES; CONSTRUCTION;
D O I
10.1039/c004037a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Quinidine was found to catalyze the Michael addition of unprotected 3-substituted oxindoles to nitroolefins in excellent yield and moderate to good diastereoselectivity. Bifunctional quinidine derived thiourea catalyst 10 could catalyze this reaction to afford the major diastereomer in up to 85% ee.
引用
收藏
页码:2912 / 2914
页数:3
相关论文
共 81 条
[1]  
Alexakis A, 2002, EUR J ORG CHEM, V2002, P3221
[2]   Organocatalytic asymmetric conjugate additions [J].
Almasi, Diana ;
Alonso, Diego A. ;
Najera, Carmen .
TETRAHEDRON-ASYMMETRY, 2007, 18 (03) :299-365
[3]   Targeting Structural and Stereochemical Complexity by Organocascade Catalysis: Construction of Spirocyclic Oxindoles Having Multiple Stereocenters [J].
Bencivenni, Giorgio ;
Wu, Li-Yuan ;
Mazzanti, Andrea ;
Giannichi, Berardino ;
Pesciaioli, Fabio ;
Song, Mao-Ping ;
Bartoli, Giuseppe ;
Melchiorre, Paolo .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (39) :7200-7203
[4]   Organocatalyzed enantioselective synthesis of nitroalkanes bearing all-carbon quaternary stereogenic centers through conjugate addition of acetone cyanohydrin [J].
Bernardi, Luca ;
Fini, Francesco ;
Fochi, Mariafrancesca ;
Ricci, Alfredo .
SYNLETT, 2008, (12) :1857-1861
[5]  
Berner OM, 2002, EUR J ORG CHEM, V2002, P1877
[6]   HETEROCYCLIC AROMATIC ANIONS WITH 4N+2-PI-ELECTRONS [J].
BORDWELL, FG ;
FRIED, HE .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (13) :4218-4223
[7]   Expanding the Scope of Cinchona Alkaloid-Catalyzed Enantioselective α-Aminations of Oxindoles: A Versatile Approach to Optically Active 3-Amino-2-oxindole Derivatives [J].
Bui, Tommy ;
Borregan, Mar ;
Barbas, Carlos F., III .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (23) :8935-8938
[8]   Thiourea-Catalyzed Highly Enantio- and Diastereoselective Additions of Oxindoles to Nitroolefins: Application to the Formal Synthesis of (+)-Physostigmine [J].
Bui, Tommy ;
Syed, Salahuddin ;
Barbas, Carlos F., III .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (25) :8758-+
[9]   Probing electronic effects in the asymmetric Heck reaction with the BIPI ligands [J].
Busacca, CA ;
Grossbach, D ;
So, RC ;
O'Brien, EM ;
Spinelli, EM .
ORGANIC LETTERS, 2003, 5 (04) :595-598
[10]   Pyrrolidine-thiourea as a bifunctional organocatalyst: Highly enantioselective Michael addition of cyclohexanone to nitroolefins [J].
Cao, Chun-Li ;
Ye, Meng-Chun ;
Sun, Xiu-Li ;
Tang, Yong .
ORGANIC LETTERS, 2006, 8 (14) :2901-2904