Mannich-type reactions in a colloidal solution formed by sodium tetrakis(3,5-trifluoromethylphenyl)borate as a catalyst in water

被引:49
作者
Chang, Chi-Tsing [1 ]
Liao, Bei-Sih [1 ]
Liu, Shiuh-Tzung [1 ]
机构
[1] Natl Taiwan Univ, Dept Chem, Taipei 106, Taiwan
关键词
AQUEOUS-MEDIA; AMINO-ACIDS; ALDEHYDES; ORGANOCATALYSIS; KETONES; SYSTEM; ALDOL;
D O I
10.1016/j.tetlet.2006.10.125
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Sodium tetrakis(3,5-trifluoromethylphenyl) borate [NaBAr4F] efficiently catalyzed the one-pot, three-component Mannich reaction of ketones with aromatic aldehydes and different anilines in water at an ambient temperature and afforded the corresponding beta-amino carbonyl compounds in good to excellent yields. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:9257 / 9259
页数:3
相关论文
共 20 条
[1]   HCl-catalyzed stereoselective Mannich reaction in H2O-SDS system [J].
Akiyama, T ;
Matsuda, K ;
Fuchibe, K .
SYNLETT, 2005, (02) :322-324
[2]   Theory of asymmetric organocatalysis of aldol and related reactions: Rationalizations and predictions [J].
Allemann, C ;
Gordillo, R ;
Clemente, FR ;
Cheong, PHY ;
Houk, KN .
ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) :558-569
[3]   Coordination of fluoro ligands toward sodium ions makes the difference: Aqua sodium ions act as Bronsted acids in polymerization of vinyl ethers and styrenes [J].
Chang, Chi-Tsing ;
Chen, Chuan-Lin ;
Liu, Yi-Hong ;
Peng, Shie-Ming ;
Chou, Pi-Tai ;
Liu, Shiuh-Tzung .
INORGANIC CHEMISTRY, 2006, 45 (19) :7590-7592
[4]   The direct catalytic asymmetric Mannich reaction [J].
Córdova, A .
ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (02) :102-112
[5]   A highly enantioselective amino acid-catalyzed route to functionalized α-amino acids [J].
Córdova, A ;
Notz, W ;
Zhong, GF ;
Betancort, JM ;
Barbas, CF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (09) :1842-1843
[6]  
GRIECO PA, 2006, ORGANIC SYNTHESIS WA, V12, P1312
[7]   Catalytic asymmetric Mannich-type reactions activated by ZnF2 chiral diamine in aqueous media [J].
Hamada, T ;
Manabe, K ;
Kobayashi, S .
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (04) :1205-1215
[8]   The direct and enantioselective, one-pot, three-component, cross-Mannich reaction of aldehydes [J].
Hayashi, Y ;
Tsuboi, W ;
Ashimine, I ;
Urushima, T ;
Shoji, M ;
Sakai, K .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (31) :3677-3680
[9]   Direct catalytic enantioselective α-aminomethylation of ketones [J].
Ibrahem, I ;
Casas, J ;
Córdova, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (47) :6528-6531
[10]   A FACILE INSITU DIAZO-COUPLING REACTIONS UNDER 2-PHASE CONDITIONS CATALYZED BY TETRAKIS[3,5-BIS(TRIFLUOROMETHYL)PHENYL]BORATE ION [J].
IWAMOTO, H ;
SONODA, T ;
KOBAYASHI, H .
TETRAHEDRON LETTERS, 1983, 24 (43) :4703-4706