C2-symmetric bicyclo[2.2.2]octadienes as chiral ligands:: Their high performance in rhodium-catalyzed asymmetric arylation of N-tosylarylimines

被引:361
作者
Tokunaga, N [1 ]
Otomaru, Y [1 ]
Okamoto, K [1 ]
Ueyama, K [1 ]
Shintani, R [1 ]
Hayashi, T [1 ]
机构
[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Kyoto 6068502, Japan
关键词
D O I
10.1021/ja044790e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Asymmetric synthesis of diarylmethylamines with high enantioselectivity (95-99% ee) was realized by use of a new C2-symmetric diene ligand, (1R,4R)-2,5-diphenylbicyclo[2.2.2]octa-2,5-diene (Ph-bod*), for the rhodium-catalyzed asymmetric arylation of N-tosylarylimines with arylboroxines. Copyright © 2004 American Chemical Society.
引用
收藏
页码:13584 / 13585
页数:2
相关论文
共 29 条
[1]   Synthesis of optically active endo,endo bicyclo[2.2.2]octane-2,5-diol, bicyclo[2.2.2]octane-2,5-dione, and related compounds [J].
Almqvist, F ;
Ekman, N ;
Frejd, T .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (11) :3794-3798
[2]  
Baltes E., 1982, Patent No. [EP58146, 58146]
[3]   AN EFFICIENT SYNTHESIS OF THE BENZHYDRYLPIPERAZINE DELTA-OPIOID AGONIST (+)-BW373U86 [J].
BISHOP, MJ ;
MCNUTT, RW .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (12) :1311-1314
[4]   High efficiency and enantioselectivity in the Rh-catalyzed conjugate addition of arylboronic acids using monodentate phosphoramidites [J].
Boiteau, JG ;
Minnaard, AJ ;
Feringa, BL .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (24) :9481-9484
[5]  
Bolm C, 2001, ANGEW CHEM INT EDIT, V40, P3285
[6]   Rhodium-catalyzed carbon-carbon bond forming reactions of organometallic compounds [J].
Fagnou, K ;
Lautens, M .
CHEMICAL REVIEWS, 2003, 103 (01) :169-196
[7]   Readily available [2.2.2]-bicyclooctadienes as new chiral ligands for Ir(I): Catalytic, kinetic resolution of allyl carbonates [J].
Fischer, C ;
Defieber, C ;
Suzuki, T ;
Carreira, EM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (06) :1628-1629
[8]   Chiral olefin Ligands - New "Spectators" in asymmetric catalysis [J].
Glorius, F .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (26) :3364-3366
[9]   A chiral chelating diene as a new type of chiral ligand for transition metal catalysts: Its preparation and use for the rhodium-catalyzed asymmetric 1,4-addition [J].
Hayashi, T ;
Ueyama, K ;
Tokunaga, N ;
Yoshida, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (38) :11508-11509
[10]   DICHLORO[1,1'-BIS(DIPHENYLPHOSPHINO)FERROCENE]PALLADIUM-(II) - AN EFFECTIVE CATALYST FOR CROSS-COUPLING OF SECONDARY AND PRIMARY ALKYL GRIGNARD AND ALKYLZINC REAGENTS WITH ORGANIC HALIDES [J].
HAYASHI, T ;
KONISHI, M ;
KOBORI, Y ;
KUMADA, M ;
HIGUCHI, T ;
HIROTSU, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (01) :158-163