Highly enantioselective iridium-catalyzed hydrogenation of heteroaromatic compounds, quinolines

被引:484
作者
Wang, WB [1 ]
Lu, SM [1 ]
Yang, PY [1 ]
Han, XW [1 ]
Zhou, YG [1 ]
机构
[1] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China
关键词
D O I
10.1021/ja0353762
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The highly enantioselective hydrogenation of quinoline derivatives is developed using [Ir(COD)Cl]2/(R)-MeO-Biphep/I2 system, and this methodology has been applied to the asymmetric synthesis of three naturally occurring alkaloids angustureine, galipinine, and cuspareine. This method provided an efficient access to a variety of optically active tetrahydroquinolines with up to 96% ee. Copyright © 2003 American Chemical Society.
引用
收藏
页码:10536 / 10537
页数:2
相关论文
共 35 条
[1]   Synthesis, absolute configuration and intermediates of 9-fluoro-6,7-dihydro-5-methyl-1-oxo-1H,5H-benzo[i,j]quinolizine-2-carboxylic acid (flumequine) [J].
Bálint, J ;
Egri, G ;
Fogassy, E ;
Böcskei, Z ;
Simon, K ;
Gajáry, A ;
Friesz, A .
TETRAHEDRON-ASYMMETRY, 1999, 10 (06) :1079-1087
[2]   HOMOGENEOUS CATALYTIC-HYDROGENATION .6. SYNTHETIC AND MECHANISTIC ASPECTS OF THE REGIOSELECTIVE REDUCTIONS OF MODEL COAL NITROGEN, SULFUR, AND OXYGEN HETEROAROMATIC-COMPOUNDS USING THE (ETA-5-PENTAMETHYLCYCLOPENTADIENYL)RHODIUM TRIS(ACETONITRILE) DICATION COMPLEX AS THE CATALYST PRECURSOR [J].
BARALT, E ;
SMITH, SJ ;
HURWITZ, J ;
HORVATH, IT ;
FISH, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (13) :5187-5196
[3]  
Barton D.H.R., 1999, Comprehensive Natural Products Chemistry, V1st
[4]   Transition metal complexes with the C1-symmetric diphosphines (R)-(R)-3-benzyl-2,4-bis(diphenylphosphino)pentane and (R)-(R)-3-benzyl(p-sulphonate)-2,4-bis(diphenylphosphino)pentane sodium salt.: Applications to enantioselective catalysis in different phase systems [J].
Bianchini, C ;
Barbaro, P ;
Scapacci, G .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 621 (1-2) :26-33
[5]  
Bianchini C, 2001, HELV CHIM ACTA, V84, P2895
[6]   Enantioselective hydrogenation of 2-methylquinoxaline to (-)-(2S)-2-methyl-1,2,3,4-tetrahydroquinoxaline by iridium catalysis [J].
Bianchini, C ;
Barbaro, P ;
Scapacci, G ;
Farnetti, E ;
Graziani, M .
ORGANOMETALLICS, 1998, 17 (15) :3308-3310
[7]   Mimicking the HDS activity of ruthenium-based catalysts 2:: The hydrogenation of benzo[b]thiophene to 2,3-dihydrobenzo [b]thiophene [J].
Bianchini, C ;
Meli, A ;
Moneti, S ;
Oberhauser, W ;
Vizza, F ;
Herrera, V ;
Fuentes, A ;
Sánchez-Delgado, RA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (30) :7071-7080
[8]   HETEROAROMATICITY .5. A UNIFIED AROMATICITY INDEX [J].
BIRD, CW .
TETRAHEDRON, 1992, 48 (02) :335-340
[9]   HOMOGENEOUS CATALYTIC-HYDROGENATION .5. REGIOSELECTIVE REDUCTIONS OF MONONUCLEAR AND POLYNUCLEAR HETEROAROMATIC MODEL COAL COMPOUNDS USING THE (ETA-5-PENTAMETHYLCYCLOPENTADIENYL)RHODIUM TRIS(ACETONITRILE) DICATION AS THE CATALYST PRECURSOR [J].
FISH, RH ;
BARALT, E ;
SMITH, SJ .
ORGANOMETALLICS, 1991, 10 (01) :54-56
[10]   HOMOGENEOUS CATALYTIC-HYDROGENATION .2. SELECTIVE REDUCTION OF POLYNUCLEAR HETEROAROMATIC-COMPOUNDS CATALYZED BY CHLOROTRIS(TRIPHENYLPHOSPHINE)RHODIUM(I) [J].
FISH, RH ;
TAN, JL ;
THORMODSEN, AD .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (23) :4500-4505