L-Proline catalysed asymmetric aldol reactions in PEG-400 as recyclable medium and transfer aldol reactions

被引:126
作者
Chandrasekhar, S [1 ]
Reddy, NR [1 ]
Sultana, SS [1 ]
Narsihmulu, C [1 ]
Reddy, KV [1 ]
机构
[1] Indian Inst Chem Technol, Hyderabad 500007, Andhra Pradesh, India
关键词
L-proline; PEG-400; aldol reaction; transfer aldol reaction;
D O I
10.1016/j.tet.2005.09.122
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
L-Proline-catalysed direct asymmetric aldol reaction of acetone with various aldehydes in PEG-400 is described. Recycling of the catalyst and solvent (PEG) was possible up to ten runs without loss of catalyst activity. L-Proline was also found to be an efficient catalyst for the asymmetric transfer aldol reaction between various aldehydes and diacetone alcohol for the first time. Good yields and enantioselectivities were observed with both methods. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:338 / 345
页数:8
相关论文
共 67 条
[51]  
2-L
[52]   Proline catalyzed aldol reactions in aqueous micelles: an environmentally friendly reaction system [J].
Peng, YY ;
Ding, QP ;
Li, ZC ;
Wang, PG ;
Cheng, JP .
TETRAHEDRON LETTERS, 2003, 44 (19) :3871-3875
[53]   Amino acid catalyzed direct asymmetric aldol reactions: A bioorganic approach to catalytic asymmetric carbon-carbon bond-forming reactions [J].
Sakthivel, K ;
Notz, W ;
Bui, T ;
Barbas, CF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (22) :5260-5267
[54]   First catalytic, enantioselective aldol-Tishchenko reactions with ketone aldols as enol equivalents [J].
Schneider, C ;
Hansch, M .
SYNLETT, 2003, (06) :837-840
[55]   MECHANISTIC STUDIES OF AN ANTIBODY-CATALYZED ELIMINATION-REACTION [J].
SHOKAT, K ;
UNO, T ;
SCHULTZ, PG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (06) :2261-2270
[56]   Aluminum enolates via retroaldol reaction: catalytic tandem aldol-transfer-Tischtschenko reaction of aldehydes with aldol adducts of ketones to ketones [J].
Simpura, I ;
Nevalainen, V .
TETRAHEDRON, 2003, 59 (38) :7535-7546
[57]   Tandem aldol-transfer-Tischtschenko reaction of aldehydes and β-hydroxyketones catalyzed by trimethylaluminum [J].
Simpura, I ;
Nevalainen, V .
TETRAHEDRON LETTERS, 2001, 42 (23) :3905-3907
[58]  
Simpura I, 2000, ANGEW CHEM INT EDIT, V39, P3422, DOI 10.1002/1521-3773(20001002)39:19<3422::AID-ANIE3422>3.0.CO
[59]  
2-U
[60]   New and stereoselective synthesis of 1,4-disubstituted buten-4-ols (homoallylic alcohol α-adducts) from the corresponding γ-isomers (3,4-disubstituted buten-4-ols) via an acid-catalyzed allyl-transfer reaction with aldehydes [J].
Sumida, S ;
Ohga, M ;
Mitani, J ;
Nokami, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (07) :1310-1313