Direct aldol reaction of trifluoroacetaldehyde ethyl hemiacetal with ketones by use of the combination of amines and acids

被引:13
作者
Funabiki, Kazumasa [1 ]
Nagaya, Hideyuki [1 ]
Ishihara, Mika [1 ]
Matsui, Masaki [1 ]
机构
[1] Gifu Univ, Fac Engn, Dept Mat Sci & Technol, Gifu 5011193, Japan
关键词
trifluoromethyl group; aldol reaction;
D O I
10.1016/j.tet.2006.03.053
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Trifluoroacetaldehyde ethyl hemiacetal reacts with unmodified ketones in the presence of 30-50 each moll % of amines and acids at ambient temperature, affording the corresponding beta-hydroxy-beta-trifluorornethylatcd ketones in good yields with good to excellent dia-stereoselectivities. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5049 / 5053
页数:5
相关论文
共 31 条
[1]   AN IMPROVED SYNTHESIS OF PERFLUOROALDEHYDES [J].
BRAID, M ;
ISERSON, H ;
LAWLOR, FE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (15) :4027-4027
[2]  
BUCCIARELLI M, 1990, GAZZ CHIM ITAL, V120, P99
[3]   SUBSTITUENT EFFECT ON THE ABSOLUTE STEREOCHEMISTRY OF THE ASYMMETRIC REDUCTION OF FLUORINE-CONTAINING BETA-DIKETONES BY BAKERS-YEAST [J].
BUCCIARELLI, M ;
FORNI, A ;
MORETTI, I ;
PRATI, F ;
TORRE, G .
BIOCATALYSIS, 1994, 9 (1-4) :313-320
[4]   Chiral phosphoramide-catalyzed aldol additions of ketone enolates. Preparative aspects [J].
Denmark, SE ;
Stavenger, RA ;
Wong, KT ;
Su, XP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (21) :4982-4991
[5]   Asymmetric aldol additions catalyzed by chiral phosphoramides: Electronic effects of the aldehyde component [J].
Denmark, SE ;
Stavenger, RA ;
Wong, KT .
TETRAHEDRON, 1998, 54 (35) :10389-10402
[6]   An efficient synthetic chiral modifier for platinum [J].
Diezi, S ;
Hess, M ;
Orglmeister, E ;
Mallat, T ;
Baiker, A .
CATALYSIS LETTERS, 2005, 102 (3-4) :121-125
[7]   Fine tuning the "chiral sites" on solid enantio selective catalysts [J].
Diezi, S ;
Mallat, T ;
Szabo, A ;
Baiker, A .
JOURNAL OF CATALYSIS, 2004, 228 (01) :162-173
[8]   STEREOCHEMICAL CONTROL IN YEAST REDUCTION OF FLUORINATED BETA-DIKETONES [J].
FORNI, A ;
MORETTI, I ;
PRATI, F ;
TORRE, G .
TETRAHEDRON, 1994, 50 (41) :11995-12000
[9]   Practical asymmetric synthesis of β-hydroxy-β-trifluoromethylated ketones via the first example of the in situ generation of trifluoroacetaldehyde and its successive asymmetric carbon-carbon bond formation reaction with chiral imines [J].
Funabiki, K ;
Hashimoto, W ;
Matsui, M .
CHEMICAL COMMUNICATIONS, 2004, (18) :2056-2057
[10]   The use of trifluoroacetaldehyde ethyl hemiacetal or hydrate in a simple and practical regioselective synthesis of β-hydroxy-β-trifluoromethyl ketones from enamines and imines [J].
Funabiki, K ;
Matsunaga, K ;
Nojiri, M ;
Hashimoto, W ;
Yamamoto, H ;
Shibata, K ;
Matsui, M .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (07) :2853-2860