One-pot synthesis of α-diazo-β-hydroxyesters under phase-transfer catalysis and application to the catalytic asymmetric aldol reaction

被引:36
作者
Arai, S [1 ]
Hasegawa, K [1 ]
Nishida, A [1 ]
机构
[1] Chiba Univ, Grad Sch Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan
关键词
Aldol reaction; ammonium salt; asymmetric synthesis; diazoester; phase transfer;
D O I
10.1016/j.tetlet.2003.11.083
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The one-pot (three steps) synthesis of alpha-diazo-beta-hydroxyesters from tosyl chloride under phase-transfer catalysis is described. The catalytic asymmetric aldol reaction between a diazoester and aldehydes was also investigated and gave moderate to good enantioselectivity. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1023 / 1026
页数:4
相关论文
共 24 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]  
[Anonymous], 1997, PHASE TRANSFER CATAL
[3]   Phase-transfer-catalyzed asymmetric Darzens reaction [J].
Arai, S ;
Shirai, Y ;
Ishida, T ;
Shioiri, T .
TETRAHEDRON, 1999, 55 (20) :6375-6386
[4]  
Bhunnoo RA, 2002, ANGEW CHEM INT EDIT, V41, P3479, DOI 10.1002/1521-3773(20020916)41:18<3479::AID-ANIE3479>3.0.CO
[5]  
2-O
[6]  
BUKOTH TL, 1969, TETRAHEDRON LETT, P5049
[7]   Highly enantioselective phase transfer catalyzed alkylation of a 3-oxygenated propionic ester equivalent; applications and mechanism [J].
Corey, EJ ;
Bo, YX ;
Busch-Petersen, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (49) :13000-13001
[8]  
Corey EJ, 1999, ANGEW CHEM INT EDIT, V38, P1931, DOI 10.1002/(SICI)1521-3773(19990712)38:13/14<1931::AID-ANIE1931>3.0.CO
[9]  
2-4
[10]   A rational approach to catalytic enantioselective enolate alkylation using a structurally rigidified and defined chiral quaternary ammonium salt under phase transfer conditions [J].
Corey, EJ ;
Xu, F ;
Noe, MC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (50) :12414-12415