Asymmetric hydrogenation of cyclic alpha,beta-unsaturated ketones to chiral allylic alcohols

被引:0
|
作者
Ohkuma, T [1 ]
Ikehira, H [1 ]
Ikariya, T [1 ]
Noyori, R [1 ]
机构
[1] RES DEV CORP JAPAN, ERATO, MOL CATALYSIS PROJECT, TOYOTA 47003, JAPAN
关键词
asymmetric hydrogenation; BINAP; chiral allylic alcohol; chiral 1,2-diamine; alpha; beta-unsaturated ketone;
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Ru(II)-BINAP-1,2-diphenylethylenediamine combined catalyst system effects asymmetric hydrogenation of certain cyclic enones in 2-propanol containing KOH with a substrate/catalyst molar ratio of 250 to 2500. The hydrogenation occurs selectively at the C=O function with excellent enantio- or diastereoselectivity.
引用
收藏
页码:467 / +
相关论文
共 50 条
  • [1] Selective reduction of alpha,beta-unsaturated aldehydes and ketones to allylic alcohols with diisobutylalkoxyalanes
    Cha, JS
    Kwon, OO
    Kwon, SY
    [J]. ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1996, 28 (03) : 355 - 359
  • [2] SELECTIVE REDUCTION OF ALPHA,BETA-UNSATURATED ALDEHYDES AND KETONES TO ALLYLIC ALCOHOLS WITH DIISOBUTYLCHLOROALANE
    CHA, JS
    KWON, OO
    KWON, SY
    [J]. BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 1995, 16 (11) : 1009 - 1011
  • [3] Enantioselective hydrogenation of alpha,beta-unsaturated cyclic ketones by double asymmetric induction preparation of (R)-muscone
    Xie, BH
    Lu, SJ
    Fu, HX
    Gao, LY
    [J]. CHINESE CHEMICAL LETTERS, 1997, 8 (06) : 477 - 478
  • [4] HYDROGENATION OF ALPHA,BETA-UNSATURATED ALDEHYDES AND KETONES TO THE UNSATURATED ALCOHOLS CATALYZED BY HYDRIDOIRIDIUM PHOSPHINE COMPLEXES
    FARNETTI, E
    PESCE, M
    KASPAR, J
    SPOGLIARICH, R
    GRAZIANI, M
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (10) : 746 - 747
  • [5] CATALYTIC ASYMMETRIC SYNTHESES .2. HYDROGENATION OF ALPHA,BETA-UNSATURATED KETONES USING CHIRAL RUTHENIUM COMPLEXES
    MASSONNEAU, V
    LEMAUX, P
    SIMONNEAUX, G
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1987, 327 (02) : 269 - 273
  • [6] SYNTHESIS OF DIACIDS AND KETO ACIDS BY RUTHENIUM TETRAOXIDE CATALYZED OXIDATION OF CYCLIC ALLYLIC ALCOHOLS AND ALPHA,BETA-UNSATURATED KETONES
    WEBSTER, FX
    RIVASENTERRIOS, J
    SILVERSTEIN, RM
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (04): : 689 - 691
  • [7] Hydrogenation of alpha,beta-unsaturated ketones on metal catalysts
    Szollosi, G
    Mastalir, A
    Molnar, A
    Bartok, M
    [J]. REACTION KINETICS AND CATALYSIS LETTERS, 1996, 57 (01): : 29 - 36
  • [8] The mechanism of oxidation of allylic alcohols to alpha,beta-unsaturated ketones by cytochrome p450
    Bellucci, G
    Chiappe, C
    Pucci, L
    Gervasi, PG
    [J]. CHEMICAL RESEARCH IN TOXICOLOGY, 1996, 9 (05) : 871 - 874
  • [9] ASYMMETRIC TRANSFER HYDROGENATION OF PROCHIRAL ALPHA,BETA-UNSATURATED ACIDS AND THEIR ESTERS BY ACHIRAL OR CHIRAL ALCOHOLS WITH RUTHENIUM CHIRAL DIPHOSPHINE COMPLEXES
    YOSHINAGA, K
    KITO, T
    OHKUBO, K
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1983, 56 (06) : 1786 - 1790
  • [10] ASYMMETRIC DIHYDROXYLATION (AD) OF ALPHA,BETA-UNSATURATED KETONES
    WALSH, PJ
    SHARPLESS, KB
    [J]. SYNLETT, 1993, (08) : 605 - 606