C2-symmetric bicyclo[3.3.1]nonadiene as a chiral ligand for rhodium-catalyzed asymmetric arylation of N-(4-nitrobenzenesulfonyl)arylimines

被引:164
作者
Otomaru, Y [1 ]
Tokunaga, N [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/ol0476063
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Asymmetric synthesis of diarylmethylamines with high enantioselectivity (95-99% ee) was realized by use of a new C-2-symmetric diene ligand. (1R,5R)-2,6-diphenylbicyclo[3.3.1]nona-2,6-diene (Ph-bnd*), for the rhodium-catalyzed asymmetric arylation of N(4-nitrobenzenesulfony)arylimines with arylboroxines.
引用
收藏
页码:307 / 310
页数:4
相关论文
共 26 条
[1]   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
[2]  
BOLM C, 2001, CHEM INT ED, V10, P3284
[3]   Chiral [2.2.2] dienes as ligands for Rh(I) in conjugate additions of boronic acids to a wide range of acceptors [J].
Defieber, C ;
Paquin, JF ;
Serna, S ;
Carreira, EM .
ORGANIC LETTERS, 2004, 6 (21) :3873-3876
[4]   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
[5]   2-NITROBENZENESULFONAMIDES AND 4-NITROBENZENESULFONAMIDES - EXCEPTIONALLY VERSATILE MEANS FOR PREPARATION OF SECONDARY-AMINES AND PROTECTION OF AMINES [J].
FUKUYAMA, T ;
JOW, CK ;
CHEUNG, M .
TETRAHEDRON LETTERS, 1995, 36 (36) :6373-6374
[6]   Chiral olefin Ligands - New "Spectators" in asymmetric catalysis [J].
Glorius, F .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (26) :3364-3366
[7]  
GREENE TW, 1999, PROTECTIVE GROUPS OR, P609
[8]   Asymmetric synthesis of diarylmethyl amines by rhodium-catalyzed asymmetric addition of aryl titanium reagents to imines [J].
Hayashi, T ;
Kawai, M ;
Tokunaga, N .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (45) :6125-6128
[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]   Rhodium-catalyzed asymmetric arylation of imines with organostannanes. Asymmetric synthesis of diarylmethylamines [J].
Hayashi, T ;
Ishigedani, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (05) :976-977