Efficient rhodium-catalyzed asymmetric hydrogenation for the synthesis of a new class of N-aryl β-amino acid derivatives

被引:83
作者
Dai, Q [1 ]
Yang, WR [1 ]
Zhang, XM [1 ]
机构
[1] Penn State Univ, Dept Chem, University Pk, PA 16802 USA
关键词
D O I
10.1021/ol0523897
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
N-Aryl beta-amino esters were obtained by asymmetric hydrogenation of a new class of N-aryl beta-enamino esters. High conversions and up to 96.3% ee values were achieved with a Rh-TangPhos catalyst.
引用
收藏
页码:5343 / 5345
页数:3
相关论文
共 22 条
[1]   Efficient synthetic method for β-enamino esters using ultrasound [J].
Brandt, CA ;
da Silva, ACMP ;
Pancote, CG ;
Brito, CL ;
da Silveira, MAB .
SYNTHESIS-STUTTGART, 2004, (10) :1557-1559
[2]   A three-step procedure for asymmetric catalytic reductive amidation of ketones [J].
Burk, MJ ;
Casy, G ;
Johnson, NB .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (18) :6084-6085
[3]   Investigating the pi-facial discrimination phenomenon in the conjugate addition of amines to chiral crotonates: A convenient basis for the rational design of chiral auxiliaries [J].
Dumas, F ;
Mezrhab, B ;
dAngelo, J ;
Riche, C ;
Chiaroni, A .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (07) :2293-2304
[4]   MECHANISM AND STEREOSELECTIVITY OF ASYMMETRIC HYDROGENATION [J].
HALPERN, J .
SCIENCE, 1982, 217 (4558) :401-407
[5]  
Hoekstra WJ, 1999, CURR MED CHEM, V6
[6]   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
[7]  
Juaristi E., 1997, ENANTIOSELECTIVE SYN
[8]   Catalytic asymmetric synthesis of both syn- and anti-β-amino alcohols [J].
Kobayashi, S ;
Ishitani, H ;
Ueno, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (02) :431-432
[9]   ASYMMETRIC HYDROGENATION OF ENAMINES WITH A CHIRAL TITANOCENE CATALYST [J].
LEE, NE ;
BUCHWALD, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (13) :5985-5986
[10]   Recent developments in the catalytic asymmetric synthesis of α- and β-amino acids [J].
Ma, JA .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (36) :4290-4299