A facile one-pot synthesis of chiral β-amino esters

被引:64
作者
Bunlaksananusorn, T [1 ]
Rampf, F [1 ]
机构
[1] Lanxess Deutsch GmbH, Fine Chem Res & Dev, D-51369 Leverkusen, Germany
关键词
reductive amination; beta-amino esters; beta-keto esters; Ru-ClMeOBIPHEP catalyst;
D O I
10.1055/s-2005-917108
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We report a facile one-pot synthesis of chiral beta-amino esters via direct reductive amination of beta-keto esters with ammonium acetate (NH4OAc) and H-2 in the presence of chiral Ru-CIMeOBIPHEP catalysts using 2,2,2-trifluoroethanol (TFE) as a solvent, leading to beta-amino esters in high yields with high enantioselectivities (up to 99% ee).
引用
收藏
页码:2682 / 2684
页数:3
相关论文
共 31 条
[1]   Progress in enantioselective catalysis assessed from an industrial point of view [J].
Blaser, HU ;
Pugin, B ;
Spindler, F .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2005, 231 (1-2) :1-20
[2]   Chiral β-amino acid derivatives via asymmetric hydrogenation [J].
Drexler, HJ ;
You, JS ;
Zhang, SL ;
Fischer, C ;
Baumann, W ;
Spannenberg, A ;
Heller, D .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2003, 7 (03) :355-361
[3]   New route to biaryl phosphanes with axial chirality as ligands for enantioselective hydrogenations [J].
Driessen-Hölscher, BD ;
Kralik, J ;
Agel, F ;
Steffens, C ;
Hu, CH .
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (08) :979-982
[4]  
Gademann K, 1999, CURR MED CHEM, V6, P905
[5]   Foldamers: A manifesto [J].
Gellman, SH .
ACCOUNTS OF CHEMICAL RESEARCH, 1998, 31 (04) :173-180
[6]   On the enantioselective hydrogenation of isomeric β-acylamido β-alkylacrylates with chiral Rh(I) complexes -: comparison of phosphine ligands and substrates [J].
Heller, D ;
Holz, J ;
Komarov, I ;
Drexler, HJ ;
You, JS ;
Drauz, K ;
Börner, A .
TETRAHEDRON-ASYMMETRY, 2002, 13 (24) :2735-2741
[7]  
Heller D, 2002, CHEM-EUR J, V8, P5196, DOI 10.1002/1521-3765(20021115)8:22<5196::AID-CHEM5196>3.0.CO
[8]  
2-P
[9]   Highly efficient synthesis of β-amino acid derivatives via asymmetric hydrogenation of unprotected enamines [J].
Hsiao, Y ;
Rivera, NR ;
Rosner, T ;
Krska, SW ;
Njolito, E ;
Wang, F ;
Sun, YK ;
Armstrong, JD ;
Grabowski, EJJ ;
Tillyer, RD ;
Spindler, F ;
Malan, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (32) :9918-9919
[10]  
JUARISTI E, 1997, ENANTIOSELECTIVE SYT