Study of the Lewis acid-promoted imines derived from addition of silylenol ethers to glyceraldehyde

被引:22
作者
Badorrey, R [1 ]
Cativiela, C [1 ]
Díaz-de-Villegas, MD [1 ]
Gálvez, JA [1 ]
机构
[1] Univ Zaragoza, CSIC,Inst Ciencia Mat Aragon, Fac Ciencias, Dept Quim Organ, E-50009 Zaragoza, Spain
关键词
asymmetric synthesis; imines; Mannich reaction;
D O I
10.1016/j.tetlet.2003.10.027
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Chiral N-benzylimines derived form D-glyceraldehyde undergo Lewis acid-promoted asymmetric Mannich reactions with O-methyl-O-trimethylsilyl dimethylketeneacetal to give beta-amino acid esters in good yields and with excellent diastereoselectivities. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:9189 / 9192
页数:4
相关论文
共 43 条
[1]   STEREOSELECTIVE SYNTHESIS OF BETA-LACTAMS BY CONDENSATION OF TITANIUM ENOLATES OF 2-PYRIDYL THIOESTERS WITH IMINES [J].
ANNUNZIATA, R ;
CINQUINI, M ;
COZZI, F ;
COZZI, PG .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (15) :4155-4162
[2]   HIGHLY DIASTEREOSELECTIVE SYNTHESIS OF BETA-LACTAMS BY ADDITION OF TITANIUM ENOLATES OF 2-PYRIDYL THIOESTERS TO CHIRAL IMINES [J].
ANNUNZIATA, R ;
CINQUINI, M ;
COZZI, F ;
COZZI, PG .
TETRAHEDRON LETTERS, 1992, 33 (08) :1113-1116
[3]  
[Anonymous], [No title captured]
[4]  
Arend M, 1999, ANGEW CHEM INT EDIT, V38, P2873, DOI 10.1002/(SICI)1521-3773(19991004)38:19<2873::AID-ANIE2873>3.0.CO
[5]  
2-P
[6]  
Arend M, 1998, ANGEW CHEM INT EDIT, V37, P1044, DOI 10.1002/(SICI)1521-3773(19980504)37:8<1044::AID-ANIE1044>3.0.CO
[7]  
2-E
[8]  
Badorrey R, 2002, EUR J ORG CHEM, V2002, P3763, DOI 10.1002/1099-0690(200211)2002:22<3763::AID-EJOC3763>3.0.CO
[9]  
2-K
[10]   Study of the reactions between vinylmagnesium bromide and imines derived from (R)-glyceraldehyde -: The key step in the stereodivergent synthesis of conveniently protected, enantiopure syn- and anti-2-amino-1,3,4-butanetriol derivatives [J].
Badorrey, R ;
Cativiela, C ;
Díaz-De-Villegas, MD ;
Díez, R ;
Gálvez, JA .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (12) :2268-2275