Enantioselective Michael reaction of ketone lithium enolates using a chiral amine ligand

被引:43
作者
Yasuda, K [1 ]
Shindo, M [1 ]
Koga, K [1 ]
机构
[1] UNIV TOKYO,FAC PHARMACEUT SCI,BUNKYO KU,TOKYO 113,JAPAN
关键词
D O I
10.1016/0040-4039(96)01367-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The enantioselective Michael reaction of ketone lithium enolates using a chiral amine ligand (1) was studied. Michael adducts (4) of up to 94% ee were obtained by the reaction between methyl ketones (2) and Michael accepters (3) having a benzylidene group. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:6343 / 6346
页数:4
相关论文
共 25 条
  • [1] A new multifunctional heterobimetallic asymmetric catalyst for Michael additions and tandem Michael-Aldol reactions
    Arai, T
    Sasai, H
    Aoe, K
    Okamura, K
    Date, T
    Shibasaki, M
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (01): : 104 - 106
  • [2] ENANTIOSELECTIVE MICHAEL-MUKAIYAMA ADDITIONS OF SILYLKETENE ACETALS TO 2-CARBOXYCYCLOPENTENONES PROMOTED BY CHIRAL TI COMPLEXES
    BERNARDI, A
    KARAMFILOVA, K
    BOSCHIN, G
    SCOLASTICO, C
    [J]. TETRAHEDRON LETTERS, 1995, 36 (08) : 1363 - 1364
  • [3] ASYMMETRIC MICHAEL ADDITIONS CATALYZED BY NI(II) AND CO(II) COMPLEXES WITH HOMOCHIRAL LIGANDS
    BOTTEGHI, C
    PAGANELLI, S
    SCHIONATO, A
    BOGA, C
    FAVA, A
    [J]. JOURNAL OF MOLECULAR CATALYSIS, 1991, 66 (01): : 7 - 21
  • [4] CHIRAL CROWN COMPLEXES CATALYZE MICHAEL ADDITION-REACTIONS TO GIVE ADDUCTS IN HIGH OPTICAL YIELDS
    CRAM, DJ
    SOGAH, GDY
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (13) : 625 - 628
  • [5] COPPER(II) IN ORGANIC-SYNTHESIS .11. EVALUATION DF THE LIGAND ARCHITECTURE ON THE EFFICIENCY OF A COPPER(II) CATALYST FOR ENANTIOSELECTIVE MICHAEL REACTIONS
    DESIMONI, G
    DUSI, G
    FAITA, G
    QUADRELLI, P
    RIGHETTI, P
    [J]. TETRAHEDRON, 1995, 51 (14) : 4131 - 4144
  • [6] ASYMMETRIC MICHAEL ADDITIONS VIA SAMP-HYDRAZONES RAMP-HYDRAZONES ENANTIOSELECTIVE 1,4-ADDITION OF METHYL KETONES TO KNOEVENAGEL ACCEPTORS
    ENDERS, D
    DEMIR, AS
    RENDENBACH, BEM
    [J]. CHEMISCHE BERICHTE-RECUEIL, 1987, 120 (10): : 1731 - 1735
  • [7] ASYMMETRIC REACTIONS OF ENAMINES WITH METHYL (E)-4-OXO-4-(2-OXO-1,3-OXAZOLIDIN-3-YL)-2-BUTENOATE BY THE USE OF A CHIRAL TITANIUM REAGENT
    HAYASHI, Y
    OTAKA, K
    SAITO, N
    NARASAKA, K
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1991, 64 (07) : 2122 - 2127
  • [8] CATALYTIC ASYMMETRIC BENZYLATION OF ACHIRAL LITHIUM ENOLATES USING A CHIRAL LIGAND FOR LITHIUM IN THE PRESENCE OF AN ACHIRAL LIGAND
    IMAI, M
    HAGIHARA, A
    KAWASAKI, H
    MANABE, K
    KOGA, K
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (19) : 8829 - 8830
  • [9] JUARISTI E, 1993, SYNTHESIS-STUTTGART, P1271
  • [10] AN ENANTIOSELECTIVE MICHAEL ADDITION OF SOFT NUCLEOPHILES TO PROCHIRAL ENONE CATALYZED BY (2-PYRROLIDYL)ALKYL AMMONIUM HYDROXIDE
    KAWARA, A
    TAGUCHI, T
    [J]. TETRAHEDRON LETTERS, 1994, 35 (47) : 8805 - 8808