Steroeselective synthesis of β-amino ketones via direct Mannich-type reactions, catalyzed with ZrOCl2•8H2O under solvent-free conditions

被引:98
作者
Eftekhari-Sis, Bagher
Abdollahifar, Amir
Hashemi, Mohammed M.
Zirak, Maryam
机构
[1] Sharif Univ Technol, Dept Chem, Tehran, Iran
[2] Tabriz Univ, Dept Organ Chem, Tabriz, Iran
关键词
direct Mannich-type reaction; beta-amino ketones; zirconium oxychloride; solvent-free conditions; SILYL ENOL ETHERS; ZIRCONIUM TETRACHLORIDE; HIGHLY EFFICIENT; ONE-POT; ASYMMETRIC REDUCTION; CARBONYL-COMPOUNDS; OXIDE PERCHLORATE; ORGANIC-SYNTHESIS; ALDEHYDES; CONDENSATION;
D O I
10.1002/ejoc.200600493
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
At room temperature, zirconium oxychloride (ZrOCl2 center dot 8H(2)O) efficiently catalyzes the direct Mannich-type reaction of a variety of in situ generated aldimines using aldehydes and anilines with ketones in a three-component reaction under solvent-free conditions. The reaction proceeds rapidly and affords the corresponding beta-amino ketones in good to high yields with good to excellent stereoselectivities. The catalyst can be recycled for subsequent reactions without any appreciable loss of efficiency. (c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006.
引用
收藏
页码:5152 / 5157
页数:6
相关论文
共 65 条
[1]   HCl-catalyzed stereoselective Mannich reaction in H2O-SDS system [J].
Akiyama, T ;
Matsuda, K ;
Fuchibe, K .
SYNLETT, 2005, (02) :322-324
[2]  
Akiyama T, 2002, ADV SYNTH CATAL, V344, P338, DOI 10.1002/1615-4169(200206)344:3/4<338::AID-ADSC338>3.0.CO
[3]  
2-O
[4]   Bismuth(III) oxide perchlorate promoted rearrangement of epoxides to aldehydes and ketones [J].
Anderson, AM ;
Blazek, JM ;
Garg, P ;
Payne, BJ ;
Mohan, RS .
TETRAHEDRON LETTERS, 2000, 41 (10) :1527-1530
[5]  
Arend M, 1998, ANGEW CHEM INT EDIT, V37, P1044, DOI 10.1002/(SICI)1521-3773(19980504)37:8<1044::AID-ANIE1044>3.0.CO
[6]  
2-E
[7]   Multiple-component condensation strategies for combinatorial library synthesis [J].
Armstrong, RW ;
Combs, AP ;
Tempest, PA ;
Brown, SD ;
Keating, TA .
ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (03) :123-131
[8]   Highly efficient one-pot three-component Mannich reaction in water catalyzed by heteropoly acids [J].
Azizi, N ;
Torkiyan, L ;
Saidi, MR .
ORGANIC LETTERS, 2006, 8 (10) :2079-2082
[9]   Pd-assisted multicomponent synthesis of heterocycles [J].
Balme, G ;
Bossharth, E ;
Monteiro, N .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (21) :4101-4111
[10]  
Bienaymé H, 2000, CHEM-EUR J, V6, P3321, DOI 10.1002/1521-3765(20000915)6:18<3321::AID-CHEM3321>3.0.CO