Enantioselective synthesis of β-hydroxy-α-amino acid esters by aldol coupling using a chiral quaternary ammonium salt as catalyst

被引:205
作者
Horikawa, M [1 ]
Busch-Petersen, J [1 ]
Corey, EJ [1 ]
机构
[1] Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
基金
美国国家卫生研究院; 美国国家科学基金会;
关键词
D O I
10.1016/S0040-4039(99)00636-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A variety of chiral beta-hydroxy-alpha-amino acids and derivatives thereof can be synthesized enantioselectively using the aldol reaction of an aldehyde, the glycinate 1 and the cinchonidine-derived catalyst 2, as indicated in Schemes 1 and 2 and Table 1. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3843 / 3846
页数:4
相关论文
共 22 条
[1]   Cyclization of a chiral oxazolidine as a key-step for the synthesis of functionalized piperidines [J].
Agami, C ;
Couty, F ;
Mathieu, H .
TETRAHEDRON LETTERS, 1996, 37 (23) :4001-4002
[2]   Total synthesis of both enantiomers of trans-beta-hydroxypipecolic acid [J].
Battistini, L ;
Zanardi, F ;
Rassu, G ;
Spanu, P ;
Pelosi, G ;
Fava, GG ;
Ferrari, MB ;
Casiraghi, G .
TETRAHEDRON-ASYMMETRY, 1997, 8 (17) :2975-2987
[3]  
BLASER D, 1991, LIEBIGS ANN CHEM, P1067
[4]   TOTAL SYNTHESIS OF BLEOMYCIN-A(2) AND RELATED AGENTS .1. SYNTHESIS AND DNA-BINDING PROPERTIES OF THE EXTENDED C-TERMINUS - TRIPEPTIDE-S, TETRAPEPTIDE-S, PENTAPEPTIDE-S, AND RELATED AGENTS [J].
BOGER, DL ;
COLLETTI, SL ;
HONDA, T ;
MENEZES, RF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (13) :5607-5618
[5]  
CALDWELL CG, 1990, SYNTHESIS-STUTTGART, P34
[6]   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
[7]  
COREY EJ, 1992, TETRAHEDRON LETT, V33, P6735
[8]   Highly enantioselective synthesis of cyclic and functionalized α-amino acids by means of a chiral phase transfer catalyst [J].
Corey, EJ ;
Noe, MC ;
Xu, F .
TETRAHEDRON LETTERS, 1998, 39 (30) :5347-5350
[9]   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
[10]   EFFICIENT CATALYTIC ASYMMETRIC ALKYLATIONS .1. ENANTIOSELECTIVE SYNTHESIS OF (+)-INDACRINONE VIA CHIRAL PHASE-TRANSFER CATALYSIS [J].
DOLLING, UH ;
DAVIS, P ;
GRABOWSKI, EJJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (02) :446-447