Rh-catalyzed asymmetric hydrogenation of γ-phthalimido-substituted α,β-unsaturated carboxylic acid esters:: An efficient enantioselective synthesis of β-aryl-γ-amino acids

被引:60
作者
Deng, Jun
Duan, Zheng-Chao
Huang, Jia-Di
Hu, Xiang-Ping [1 ]
Wang, Dao-Yong
Yu, Sai-Bo
Xu, Xue-Feng
Zheng, Zhuo
机构
[1] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China
[2] Chinese Acad Sci, Grad Sch, Beijing 100039, Peoples R China
关键词
D O I
10.1021/ol702193v
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of chiral beta-aryl-gamma-amino acid ester derivatives were synthesized in high enantioselectivities (93-97% ee) via the Rh-catalyzed asymmetric hydrogenation of gamma-phthalimido-alpha,beta-unsaturated carboxylic acid esters using highly modular chiral BoPhoz-type phosphine-aminophosphine ligands. The method has been applied successfully to the synthesis of several chiral pharmaceuticals including (R)-baclofen and (R)-rolipram with high enantioselectivities.
引用
收藏
页码:4825 / 4828
页数:4
相关论文
共 39 条
[1]   Very efficient phosphoramidite ligand for asymmetric iridium-catalyzed allylic alkylation [J].
Alexakis, A ;
Polet, D .
ORGANIC LETTERS, 2004, 6 (20) :3529-3532
[2]   Self-assembled peptide tubelets with 7 Å pores [J].
Amorín, M ;
Castedo, L ;
Granja, JR .
CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (22) :6543-6551
[3]   New cyclic peptide assemblies with hydrophobic cavities:: The structural and thermodynamic basis of a new class of peptide nanotubes [J].
Amorín, M ;
Castedo, L ;
Granja, JR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (10) :2844-2845
[4]  
Anada M, 1999, SYNLETT, P1775
[5]   Enantioselective synthesis of 4-substituted 2-pyrrolidinones by site-selective C-H insertion of α-methoxycarbonyl-α-diazoacetanilides catalyzed by dirhodium(II) tetrakis[N-phthaloyl-(S)-tert-leucinate] [J].
Anada, M ;
Hashimoto, S .
TETRAHEDRON LETTERS, 1998, 39 (1-2) :79-82
[6]   Helix formation in α,γ- and β,γ-hybrid peptides:: Theoretical insights into mimicry of α- and β-Peptides [J].
Baldauf, C ;
Günther, R ;
Hofmann, HJ .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (03) :1200-1208
[7]  
Barluenga J, 2001, CHEM-EUR J, V7, P3533, DOI 10.1002/1521-3765(20010817)7:16<3533::AID-CHEM3533>3.0.CO
[8]  
2-E
[9]   Development of a catalytic enantioselective conjugate addition of 1,3-dicarbonyl compounds to nitroalkenes for the synthesis of endothelin-A antagonist ABT-546. Scope, mechanism, and further application to the synthesis of the antidepressant rolipram [J].
Barnes, DM ;
Ji, JG ;
Fickes, MG ;
Fitzgerald, MA ;
King, SA ;
Morton, HE ;
Plagge, FA ;
Preskill, M ;
Wagaw, SH ;
Wittenberger, SJ ;
Zhang, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (44) :13097-13105
[10]   THE CRYSTAL-STRUCTURE, ABSOLUTE-CONFIGURATION, AND PHOSPHODIESTERASE INHIBITORY ACTIVITY OF (+)-1-(4-BROMOBENZYL)-4-(3-(CYCLOPENTYLOXY)-4-METHOXYPHENYL)-PYRROLIDIN-2-ONE [J].
BAURES, PW ;
EGGLESTON, DS ;
ERHARD, KF ;
CIESLINSKI, LB ;
TORPHY, TJ ;
CHRISTENSEN, SB .
JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (22) :3274-3277