Electron deficiency of aldehydes controls the pyrrolidine catalyzed direct cross-aldol reaction of aromatic/heterocyclic aldehydes and ketones in water

被引:57
作者
Chimni, SS [1 ]
Mahajan, D [1 ]
机构
[1] Guru Nanak Dev Univ, Dept Chem, Amritsar 143005, Punjab, India
关键词
pyrrolidine catalysis; heterocyclic aldol; cross-aldol; aqueous medium; beta-hydroxy ketones;
D O I
10.1016/j.tet.2005.03.045
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A synthetically useful pyrrolidine catalyzed direct cross-aldol reaction of aromatic/heterocyclic aldehydes with ketones in water affords the aldol addition product in up to 93% yield. Electrophilicity of the aldehydes controls the course of the reaction. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5019 / 5025
页数:7
相关论文
共 50 条
[1]  
AGAMI C, 1987, B SOC CHIM FR, P358
[2]  
ALVAREZIBARRA C, 1992, J CHEM RES S, V326, P2674
[3]   MECHANISTIC INSIGHTS FROM AB-INITIO CALCULATIONS ON A NITROGEN ANALOG OF THE BORON MEDIATED ALDOL REACTION [J].
BERNARDI, A ;
GENNARI, C ;
GOODMAN, JM ;
LEUE, V ;
PATERSON, I .
TETRAHEDRON, 1995, 51 (16) :4853-4866
[4]   Direct catalytic asymmetric aldol reactions of aldehydes [J].
Bogevig, A ;
Kumaragurubaran, N ;
Jorgensen, KA .
CHEMICAL COMMUNICATIONS, 2002, (06) :620-621
[5]   Iminium ion catalysis:: Use of the α-effect in the acceleration of the Diels-Alder reaction [J].
Cavill, JL ;
Peters, JU ;
Tomkinson, NCO .
CHEMICAL COMMUNICATIONS, 2003, (06) :728-729
[6]   Direct organocatalytic aldol reactions in buffered aqueous media [J].
Córdova, A ;
Notz, W ;
Barbas, CF .
CHEMICAL COMMUNICATIONS, 2002, (24) :3024-3025
[7]   Proline-catalyzed one-step asymmetric synthesis of 5-hydroxy-(2E)-hexenal from acetaldehyde [J].
Córdova, A ;
Notz, W ;
Barbas, CF .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (01) :301-303
[8]   Mineral catalysis of a potentially prebiotic aldol condensation [J].
De Graaf, RM ;
Visscher, J ;
Xu, Y ;
Arrhenius, G ;
Schwartz, AW .
JOURNAL OF MOLECULAR EVOLUTION, 1998, 47 (05) :501-507
[9]   REACTIONS IN THE FORMOL BIOID - THE ORIGIN OF THE BRANCHED CHAINS OF ISOPRENOIDS, VALINE, AND LEUCINES [J].
DECKER, P ;
SCHWEER, H .
ORIGINS OF LIFE AND EVOLUTION OF THE BIOSPHERE, 1984, 14 (1-4) :335-342
[10]   Aqueous aldol catalysis by a nicotine metabolite [J].
Dickerson, TJ ;
Janda, KD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (13) :3220-3221