Asymmetric hydroarylation of norbornene derivatives catalyzed by palladium complexes of chiral quinolinyl-oxazolines

被引:37
作者
Wu, XY
Xu, HD
Tang, FY
Zhou, QL [1 ]
机构
[1] E China Univ Sci & Technol, Inst Fine Chem, Shanghai 200237, Peoples R China
[2] Nankai Univ, State Key Lab, Tianjin 300071, Peoples R China
[3] Nankai Univ, Inst Elementoorgan Chem, Tianjin 300071, Peoples R China
基金
中国国家自然科学基金;
关键词
D O I
10.1016/S0957-4166(01)00436-0
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Chiral quinolinyl-oxazolines were found to be efficient ligands in the enantioselective palladium-catalyzed Heck-type hydroarylation of norbornene and its derivatives. The ligands with a medium sized alkyl group on the oxazoline ring provided higher enantioselectivities. The presence of elect ron-don ati ng substituents on the aryl iodide increased the selectivity and the yield of the reactions. The configuration of (-)-exo-2-phenylbicyclo[2.2.1]heptane has been assigned as (1R, 2'R). (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2565 / 2569
页数:5
相关论文
共 27 条
[1]   PALLADIUM-CATALYZED PREPARATION OF EXO-ARYL DERIVATIVES OF THE NORBORNANE SKELETON [J].
ARCADI, A ;
MARINELLI, F ;
BERNOCCHI, E ;
CACCHI, S ;
ORTAR, G .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1989, 368 (02) :249-256
[2]  
BRUNNER H, 1991, SYNTHESIS-STUTTGART, P1121
[3]   ASYMMETRIC CATALYSIS .45. ENANTIOSELECTIVE HYDROSILYLATION OF KETONES WITH [RH(COD)CL]2/PYRIDINYLOXAZOLINE CATALYSTS [J].
BRUNNER, H ;
OBERMANN, U .
CHEMISCHE BERICHTE-RECUEIL, 1989, 122 (03) :499-507
[4]  
BUCKINGHAM J, 1982, DICT ORGANIC COMPOUN, V1, P645
[5]   THE PALLADIUM-CATALYZED CONJUGATE ADDITION TYPE REACTION OF ARYL IODIDES WITH ALPHA,BETA-UNSATURATED ALDEHYDES [J].
CACCHI, S ;
LATORRE, F ;
PALMIERI, G .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1984, 268 (02) :C48-C51
[6]   PALLADIUM-CATALYZED CONJUGATE ADDITION TYPE REACTION OF ARYL IODIDES WITH ALPHA,BETA-UNSATURATED KETONES [J].
CACCHI, S ;
ARCADI, A .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (23) :4236-4240
[7]   A GREATLY IMPROVED PROCEDURE FOR RUTHENIUM TETRAOXIDE CATALYZED OXIDATIONS OF ORGANIC-COMPOUNDS [J].
CARLSEN, PHJ ;
KATSUKI, T ;
MARTIN, VS ;
SHARPLESS, KB .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (19) :3936-3938
[8]   BIS(OXAZOLINES) AS CHIRAL LIGANDS IN METAL-CATALYZED ASYMMETRIC REACTIONS - CATALYTIC, ASYMMETRIC CYCLOPROPANATION OF OLEFINS [J].
EVANS, DA ;
WOERPEL, KA ;
HINMAN, MM ;
FAUL, MM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (02) :726-728
[9]   Chiral P,N-ligands based on ketopinic acid in the asymmetric heck reaction [J].
Gilbertson, SR ;
Fu, Z .
ORGANIC LETTERS, 2001, 3 (02) :161-164
[10]   The asymmetric cyclohexenylation of 2,2-dimethyl-2,3-dihydrofuran [J].
Hennessy, AJ ;
Malone, YM ;
Guiry, PJ .
TETRAHEDRON LETTERS, 2000, 41 (13) :2261-2264