CONJUGATE ADDITION OF DIETHYLZINC TO ENONES CATALYZED BY HOMOGENEOUS AND SUPPORTED CHIRAL NI-COMPLEXES - COOPERATIVE EFFECT OF THE SUPPORT ON ENANTIOSELECTIVITY

被引:63
作者
CORMA, A
IGLESIAS, M
MARTIN, MV
RUBIO, J
SANCHEZ, F
机构
[1] INST QUIM ORGAN J DE LA CIERVA 3,E-28006 MADRID,SPAIN
[2] INST MAT,E-28006 MADRID,SPAIN
[3] INST TECNOL QUIM,E-46071 VALENCIA,SPAIN
关键词
D O I
10.1016/S0957-4166(00)82180-1
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Chiral t-butylaminocarbonylpyrrolidine acetylacetonate Ni(II) hexafluorophosphate and the corresponding supported complexes on silica and on a modified USY-zeolite are readily prepared. The application of these free and supported complexes as catalysts in the addition Of diethylzinc to a series of different substituted enones affords chiral beta-ethylated ketones in high yields with an enantiomeric excess up to 95%.
引用
收藏
页码:845 / 848
页数:4
相关论文
共 11 条
[1]   OPTICALLY-ACTIVE BIPYRIDINES IN NICKEL CATALYZED ENANTIOSELECTIVE CONJUGATE ADDITION TO ENONES [J].
BOLM, C ;
EWALD, M .
TETRAHEDRON LETTERS, 1990, 31 (35) :5011-5012
[2]  
BOLM C, ORGANIC SYNTHESIS VI, P223
[3]   SILICA-SUPPORTED CYCLOPENTADIENYL-RHODIUM(I), CYCLOPENTADIENYL-COBALT(I), AND CYCLOPENTADIENYL-TITANIUM(IV) COMPLEXES [J].
BOOTH, BL ;
OFUNNE, GC ;
STACEY, C ;
TAIT, PJT .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1986, 315 (02) :143-156
[4]  
BRIENNE J, 1969, B SOC CHIM FR, P613
[5]  
CORMA A, IN PRESS J ORGANOMET
[6]  
COTTON FA, 1988, ADV INORG CHEM RAD, P741
[7]   EFFICIENT SYNTHESES OF (+/-)-BETA-CUPARENONE - CONJUGATE ADDITION OF ORGANOZINC REAGENTS [J].
GREENE, AE ;
LANSARD, JP ;
LUCHE, JL ;
PETRIER, C .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (05) :931-932
[8]   ENANTIOSELECTIVE CONJUGATE ADDITION OF GRIGNARD-REAGENTS TO ENONES CATALYZED BY CHIRAL ZINC(II) COMPLEXES [J].
JANSEN, JFGA ;
FERINGA, BL .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (13) :4168-4175
[9]   CATALYTIC ASYMMETRIC-SYNTHESIS OF ALKYL SUBSTITUTED LACTONES BY ENANTIOSELECTIVE AND CHEMOSELECTIVE ALKYLATION OF FORMYLESTERS WITH DIALKYLZINCS USING N,N-DIBUTYLNOREPHEDRINE [J].
SOAI, K ;
YOKOYAMA, S ;
HAYASAKA, T ;
EBIHARA, K .
CHEMISTRY LETTERS, 1988, (05) :843-846
[10]   ENANTIOSELECTIVE CONJUGATE ADDITION OF DIETHYLZINC TO ENONES USING CHIRAL BETA-AMINOALCOHOL AS CHIRAL CATALYST OR LIGAND [J].
SOAI, K ;
OKUDO, M ;
OKAMOTO, M .
TETRAHEDRON LETTERS, 1991, 32 (01) :95-96