Trifluoromethylated amino alcohols as chiral ligands for highly enantioselective Reformatsky reaction

被引:42
作者
Fujiwara, Y [1 ]
Katagiri, T [1 ]
Uneyama, K [1 ]
机构
[1] Okayama Univ, Fac Engn, Dept Appl Chem, Okayama 7008530, Japan
关键词
trifluoromethylated amino alcohol; chiral ligand; enantioselective Reformatsky reaction;
D O I
10.1016/S0040-4039(03)01392-3
中图分类号
O62 [有机化学];
学科分类号
070303 [有机化学]; 081704 [应用化学];
摘要
The enantioselective Reformatsky reaction of PhCHO was achieved by the use of trifluoromethylated amino alcohols as chiral ligands to afford the corresponding optically active beta-hydroxy ester with up to 90% ee. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6161 / 6163
页数:3
相关论文
共 28 条
[1]
Enantioselective reformatsky reaction induced by chiral beta-amino alcohols [J].
Andres, JM ;
Martin, Y ;
Pedrosa, R ;
PerezEncabo, A .
TETRAHEDRON, 1997, 53 (10) :3787-3794
[2]
Andres JM, 1996, SYNTHESIS-STUTTGART, P1070
[3]
Synthesis of chiral, non-racemic aldols from chiral β-hydroxy-Weinreb amides prepared by enantioselective Reformatsky-like reaction induced by chiral β-aminoalcohols [J].
Andrés, JM ;
Pedrosa, R ;
Pérez-Encabo, A .
TETRAHEDRON, 2000, 56 (09) :1217-1223
[4]
Diastereoselective synthesis of enantiopure γ-amino-β-hydroxy acids by Reformatsky reaction of chiral α-dibenzylamino aldehydes [J].
Andrés, JM ;
Pedrosa, R ;
Pérez, A ;
Pérez-Encabo, A .
TETRAHEDRON, 2001, 57 (40) :8521-8530
[5]
BRAUN M, 1995, LIEBIGS ANN, P1447
[6]
THE STRUCTURE OF THE REFORMATSKY REAGENT [J].
DEKKER, J ;
BOERSMA, J ;
VANDERKERK, GJM .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (10) :553-555
[7]
Asymmetric Samarium-Reformatsky reaction of chiral α-bromoacetyl-2-oxazolidinones with aldehydes [J].
Fukuzawa, S ;
Matsuzawa, H ;
Yoshimitsu, S .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (06) :1702-1706
[8]
FURSTNER A, 1989, SYNTHESIS-STUTTGART, P571
[9]
The chromium-reformatsky reaction: Asymmetric synthesis of the aldol fragment of the cytotoxic epothilons from 3-(2-bromoacyl)-2-oxazolidinones [J].
Gabriel, T ;
Wessjohann, L .
TETRAHEDRON LETTERS, 1997, 38 (08) :1363-1366
[10]
ENANTIOSELECTIVE SYNTHESIS OF BETA-HYDROXY ESTERS BY INDIUM-INDUCED REFORMATSKY REACTION [J].
JOHAR, PS ;
ARAKI, S ;
BUTSUGAN, Y .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (06) :711-713