AN IMPROVED DIPHOSPHINE-IRIDIUM(I) CATALYST SYSTEM FOR THE ASYMMETRIC HYDROGENATION OF CYCLIC IMINES - PHTHALIMIDE AS AN EFFICIENT COCATALYST

被引:85
作者
MORIMOTO, T
ACHIWA, K
机构
[1] School of Pharmaceutical Sciences, University of Shizuoka, Shizuoka-shi, 422
关键词
D O I
10.1016/0957-4166(95)00351-O
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The asymmetric hydrogenation of cyclic ketimines, 1-alkyl-3,4-dihydroisoquinolines 5a,b, was carried out with diphosphine-iridium(I) complex catalysts in the presence of various imides or amides as a co-catalyst. Remarkable effects of five-membered imides on the enantioselectivity and the catalytic activity were observed. The enantioselectivity with a BCPM 1-iridium(I) complex was much improved up to 93% ee by addition of phthalimide.
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页码:2661 / 2664
页数:4
相关论文
共 23 条
[1]   TRANSITION-METAL COMPLEXES WITH TERMINAL OR BRIDGING IMIDATO(1-) LIGANDS - X-RAY CRYSTAL-STRUCTURES OF TRANS-[IR(CO)(NCOC2F4CO)(PPH3)2] AND [(PD(ORTHO-C6H4CH=NPH)(MU-NCOC2H4CO))2].CH2CL2, SPECTROSCOPIC STUDIES OF [MN(CO)5(NCOC2H4CO)], AND THE NATURE OF THE METAL-NITROGEN BOND [J].
ADAMS, H ;
BAILEY, NA ;
BRIGGS, TN ;
MCCLEVERTY, JA ;
COLQUHOUN, HM ;
WILLIAMS, DJ .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1986, (04) :813-819
[2]  
[Anonymous], 1994, ASYMMETRIC CATALYSIS
[3]   RHODIUM(I) SULFONATED-BDPP CATALYZED ASYMMETRIC HYDROGENATION OF IMINES IN AQUEOUS ORGANIC 2-PHASE SOLVENT SYSTEMS [J].
BAKOS, J ;
OROSZ, A ;
HEIL, B ;
LAGHMARI, M ;
LHOSTE, P ;
SINOU, D .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (23) :1684-1685
[4]   A FACILE METHOD FOR THE PREPARATION OF 2,4-BIS(DIPHENYLPHOSPHINO)PENTANE (BDPP) ENANTIOMERS AND THEIR APPLICATION IN ASYMMETRIC HYDROGENATION [J].
BAKOS, J ;
TOTH, I ;
HEIL, B ;
MARKO, L .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1985, 279 (1-2) :23-29
[5]   CHEMICAL CORRELATION OF THE ABSOLUTE CONFIGURATIONS OF SALSOLIDINE, SALSOLINE, AND CALYCOTOMINE WITH THE AMINO-ACIDS [J].
BATTERSBY, AR ;
EDWARDS, TP .
JOURNAL OF THE CHEMICAL SOCIETY, 1960, (MAR) :1214-1221
[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]  
CHAN YNC, 1990, J AM CHEM SOC, V112, P9400
[8]  
INOGUCHI K, 1992, SYNLETT, P169
[9]   ASYMMETRIC REDUCTION CATALYZED BY TRANSITION-METAL COMPLEXES .4. SYNTHESIS OF CHIRAL AMINES BY MEANS OF RHODIUM COMPLEX AND 2,3-DIHYDROXY BIS(DIPHENYLPHOSPHINO)-1,4-BUTANE(DIOP) OF ISOPROPYLIDENE [J].
KAGAN, HB ;
LANGLOIS, N ;
DANG, TP .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1975, 90 (03) :353-365
[10]   RHODIUM(I)-CATALYZED ASYMMETRIC HYDROGENATION OF IMINES [J].
KANG, GJ ;
CULLEN, WR ;
FRYZUK, MD ;
JAMES, BR ;
KUTNEY, JP .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (22) :1466-1467