One-pot preparation of chiral β-amino esters by rhodium-catalyzed three-components coupling reaction

被引:48
作者
Honda, T [1 ]
Wakabayashi, H [1 ]
Kanai, K [1 ]
机构
[1] Hoshi Univ, Fac Pharmaceut Sci, Shinagawa Ku, Tokyo 1428501, Japan
关键词
chiral beta-amino ester; reformatsky reaction; rhodium-catalyzed coupling reaction; Wilkinson's catalyst; diethylzinc;
D O I
10.1248/cpb.50.307
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Chiral beta-amino esters are synthesized in one-pot from three components, amines, aldehydes, and ethyl bromoacetate, under the rhodium-catalyzed Reformatasky-type reaction condition, where complete diastereoselection is achieved in the nucleophilic addition step of ethyl bromoacetate to the imine prepared in situ.
引用
收藏
页码:307 / 308
页数:2
相关论文
共 21 条
[1]   β-amino esters via the Reformatsky reaction:: Restraining effects of the ortho-methoxyphenyl substituent [J].
Adrian, JC ;
Barkin, JL ;
Hassib, L .
TETRAHEDRON LETTERS, 1999, 40 (13) :2457-2460
[2]   A CONCISE ENANTIOSELECTIVE SYNTHESIS OF ALLYLAMINES AND N-BOC-BETA-AMINO ACIDS [J].
ALCON, M ;
CANAS, M ;
POCH, M ;
MOYANO, A ;
PERICAS, MA ;
RIERA, A .
TETRAHEDRON LETTERS, 1994, 35 (10) :1589-1592
[3]   STEREOSELECTIVE RING-OPENING OF CHIRAL OXAZOLIDINES BY REFORMATSKY REAGENTS - AN ENANTIOSELECTIVE ENTRY TO BETA-AMINO ESTERS [J].
ANDRES, C ;
GONZALEZ, A ;
PEDROSA, R ;
PEREZENCABO, A .
TETRAHEDRON LETTERS, 1992, 33 (20) :2895-2898
[4]   beta-peptide foldamers: Robust Helix formation in a new family of beta-amino acid oligomers [J].
Appella, DH ;
Christianson, LA ;
Karle, IL ;
Powell, DR ;
Gellman, SH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (51) :13071-13072
[5]  
Boge T. C., 1996, ENANTIOSELECTIVE SYN, P1
[6]   Stereoselective reduction of enantiopure beta-enamino esters by hydride: A convenient synthesis of both enantiopure beta-amino esters [J].
Cimarelli, C ;
Palmieri, G .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (16) :5557-5563
[7]  
COLE DC, 1994, TETRAHEDRON, V50, P9517
[8]   ASYMMETRIC-SYNTHESIS OF R-BETA-AMINO BUTANOIC ACID AND S-BETA-TYROSINE - HOMOCHIRAL LITHIUM AMIDE EQUIVALENTS FOR MICHAEL ADDITIONS TO ALPHA,BETA-UNSATURATED ESTERS [J].
DAVIES, SG ;
ICHIHARA, O .
TETRAHEDRON-ASYMMETRY, 1991, 2 (03) :183-186
[9]  
GRAF E, 1959, LIEBIGS ANN CHEM, V613, P111
[10]   DIASTEREOSELECTIVE ADDITION OF ORGANOMETALLIC REAGENTS TO CHIRAL IMINES AND 1,3-OXAZOLIDINES [J].
HIGASHIYAMA, K ;
INOUE, H ;
TAKAHASHI, H .
TETRAHEDRON LETTERS, 1992, 33 (02) :235-238