Stereoselective Michael addition of trimethyl aluminium to nitro acrylates: a route to 2-methyl-3-amino propionic acid

被引:44
作者
Eilitz, U [1 ]
Lessmann, F [1 ]
Seidelmann, O [1 ]
Wendisch, V [1 ]
机构
[1] ChiroBlock Ltd, D-06766 Wolfen, Germany
关键词
D O I
10.1016/S0957-4166(03)00575-5
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The copper(I)-catalysed Michael addition of trimethyl aluminium to nitro acrylates yields 2-methyl-3-nitro propionic acid esters on a 200 g scale with enantiomeric excesses up to 92%. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3095 / 3097
页数:3
相关论文
共 35 条
[1]  
Abele S, 2000, EUR J ORG CHEM, V2000, P1
[2]   Dramatic improvement of the enantiomeric excess in the asymmetric conjugate addition reaction using new experimental conditions [J].
Alexakis, A ;
Benhaim, C ;
Rosse, S ;
Humam, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (19) :5262-5263
[3]   Acceleration of the conjugate addition of diethyl zinc to enones by either Cu(OTf)(2) or trivalent phosphorus ligands [J].
Alexakis, A ;
Vastra, J ;
Mangeney, P .
TETRAHEDRON LETTERS, 1997, 38 (44) :7745-7748
[4]   Asymmetric conjugate addition of diethyl zinc to enones with tartrate chiral phosphite ligands [J].
Alexakis, A ;
Vastra, J ;
Burton, J ;
Mangeney, P .
TETRAHEDRON-ASYMMETRY, 1997, 8 (19) :3193-3196
[5]  
[Anonymous], 1994, Aldrichimica Acta
[6]  
Berner OM, 2002, EUR J ORG CHEM, V2002, P1877
[7]   β-peptides:: From structure to function [J].
Cheng, RP ;
Gellman, SH ;
DeGrado, WF .
CHEMICAL REVIEWS, 2001, 101 (10) :3219-3232
[8]  
Davies HML, 2002, ANGEW CHEM INT EDIT, V41, P2197, DOI 10.1002/1521-3773(20020617)41:12<2197::AID-ANIE2197>3.0.CO
[9]  
2-N
[10]   Copper-catalysed asymmetric 1,4-addition of organometallic reagents to 2-cyclohexenone using novel phosphine-phosphite ligands [J].
Diéguez, M ;
Deerenberg, S ;
Pàmies, O ;
Claver, C ;
van Leeuwen, PWNM ;
Kamer, P .
TETRAHEDRON-ASYMMETRY, 2000, 11 (15) :3161-3166