Highly enantioselective reductive amination of simple aryl ketones catalyzed by Ir-f-Binaphane in the presence of titanium(IV) isopropoxide and iodine

被引:159
作者
Chi, YX [1 ]
Zhou, YG [1 ]
Zhang, XM [1 ]
机构
[1] Penn State Univ, Dept Chem, University Pk, PA 16802 USA
关键词
D O I
10.1021/jo026856z
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Using an Ir-f-Binaphane complex as the catalyst, complete conversions and high enantioselectivies (up to 96% ee) were achieved in the asymmetric reductive amination of aryl ketones in the presence of Ti((OPr)-Pr-i)(4) and I-2. A simple and efficient method of synthesizing chiral primary amines has been realized.
引用
收藏
页码:4120 / 4122
页数:3
相关论文
共 42 条
[1]   Pd-catalyzed asymmetric hydrogenation of α-fluorinated iminoesters in fluorinated alcohol:: A new and catalytic enantioselective synthesis of fluoro α-amino acid derivatives [J].
Abe, H ;
Amii, H ;
Uneyama, K .
ORGANIC LETTERS, 2001, 3 (03) :313-315
[2]  
Blaser H.-U., 1999, COMPREHENSIVE ASYMME, P247
[3]  
Blaser HU, 1999, SYNLETT, P867
[4]   Tunable ferrocenyl diphosphine ligands for the Ir-catalyzed enantioselective hydrogenation of N-aryl imines [J].
Blaser, HU ;
Buser, HP ;
Häusel, R ;
Jalett, HP ;
Spindler, F .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 621 (1-2) :34-38
[5]  
Brown J. M, 1999, COMPREHENSIVE ASYMME, VI, P121
[6]   ENANTIOSELECTIVE HYDROGENATION OF THE C=N GROUP - A CATALYTIC ASYMMETRIC REDUCTIVE AMINATION PROCEDURE [J].
BURK, MJ ;
FEASTER, JE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (15) :6266-6267
[7]   CATALYTIC ASYMMETRIC REDUCTIVE AMINATION OF KETONES VIA HIGHLY ENANTIOSELECTIVE HYDROGENATION OF THE C=N DOUBLE-BOND [J].
BURK, MJ ;
MARTINEZ, JP ;
FEASTER, JE ;
COSFORD, N .
TETRAHEDRON, 1994, 50 (15) :4399-4428
[8]   The application of Ir-complexes of trans-2,5-dialkylpyrrolidinyl-benzyldiphenylphosphines to the enantioselective reduction of imines [J].
Cahill, JP ;
Lightfoot, AP ;
Goddard, R ;
Rust, J ;
Guiry, PJ .
TETRAHEDRON-ASYMMETRY, 1998, 9 (24) :4307-4312
[9]   A method for the asymmetric hydrosilylation of N-aryl imines [J].
Hansen, MC ;
Buchwald, SL .
ORGANIC LETTERS, 2000, 2 (05) :713-715
[10]   Asymmetric reduction of imines [J].
Hashiguchi, S ;
Uematsu, N ;
Noyori, R .
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1997, 55 (02) :99-109