Chiral ligand-controlled asymmetric conjugate addition of lithium amides to enoates

被引:100
作者
Doi, H [1 ]
Sakai, T [1 ]
Iguchi, M [1 ]
Yamada, K [1 ]
Tomioka, K [1 ]
机构
[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan
关键词
D O I
10.1021/ja029633z
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The external chiral ligand-controlled asymmetric conjugate addition reaction of lithium amides with α,β-unsaturated esters provided β-amino esters in high yields and high enantioselectivities. Copyright © 2003 American Chemical Society.
引用
收藏
页码:2886 / 2887
页数:2
相关论文
共 57 条
[21]   ASYMMETRIC MICHAEL REACTIONS OF 3,5-DIHYDRO-4H-DINAPHTH[2,1-C-1',2'-E]AZEPINE WITH METHYL CROTONATE [J].
HAWKINS, JM ;
FU, GC .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (14) :2820-2822
[22]   THE CHEMISTRY OF ACTIVATED BLEOMYCIN [J].
HECHT, SM .
ACCOUNTS OF CHEMICAL RESEARCH, 1986, 19 (12) :383-391
[23]  
JAURISTI E, 1997, ENANTIOSELECTIVE SYN
[24]   Highly diastereoselective and enantioselective carbon-carbon bond formations in conjugate additions of lithiated N-boc allylamines to nitroalkenes:: Enantioselective synthesis of 3,4-and 3,4,5-substituted piperidines including (-)-paroxetine [J].
Johnson, TA ;
Curtis, MD ;
Beak, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (05) :1004-1005
[25]   CATALYTIC ASYMMETRIC CONJUGATE ADDITION OF GRIGNARD-REAGENTS MEDIATED BY COPPER(I)-CHIRAL BIDENTATE PHOSPHINE COMPLEX [J].
KANAI, M ;
TOMIOKA, K .
TETRAHEDRON LETTERS, 1995, 36 (24) :4275-4278
[26]  
Krause N, 2001, SYNTHESIS-STUTTGART, P171
[27]   Hemilabile amidomonophosphine ligand-rhodium(I) complex-catalyzed asymmetric 1,4-addition of arylboronic acids to cycloalkenones [J].
Kuriyama, M ;
Nagai, K ;
Yamada, K ;
Miwa, Y ;
Taga, T ;
Tomioka, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (30) :8932-8939
[28]   Enantioselective synthesis of α,α-disubstituted amines from nitroalkenes [J].
Leroux, ML ;
Le Gall, T ;
Mioskowski, C .
TETRAHEDRON-ASYMMETRY, 2001, 12 (13) :1817-1823
[29]   Recent advances in the stereoselective synthesis of β-amino acids [J].
Liu, M ;
Sibi, MP .
TETRAHEDRON, 2002, 58 (40) :7991-8035
[30]  
LUKACS G, 1990, RECENT PROGR CHEM SY