Diphenylprolinol methyl ether: A highly enantioselective catalyst for Michael addition of aldehydes to simple enones

被引：223
作者：
Chi, YG [1 ]
Gellman, SH [1 ]
机构：
[1] Univ Wisconsin, Dept Chem, Madison, WI 53706 USA
来源：
ORGANIC LETTERS | 2005年 / 7卷 / 19期
关键词：
D O I：
10.1021/ol0517729
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Diphenylprolinol methyl ether catalyzes intermolecular Michael addition of simple aldehydes to relatively nonactivated enones with the highest enantioselectivities reported to date (95-99% ee) and significantly lower catalyst loadings than have been,typical in this arena.
引用
收藏
页码：4253 / 4256
页数：4
相关论文
共 46 条
  • [1] Asymmetric Michael addition of α-hydroxyketones to nitroolefins catalyzed by chiral diamine
    Andrey, O
    Alexakis, A
    Bernardinelli, G
    [J]. ORGANIC LETTERS, 2003, 5 (14) : 2559 - 2561
  • [2] [Anonymous], [No title captured]
  • [3] Catalytic direct asymmetric Michael reactions: Addition of unmodified ketone and aldehyde donors to alkylidene malonates and nitro olefins
    Betancort, JM
    Sakthivel, K
    Thayumanavan, R
    Tanaka, F
    Barbas, CF
    [J]. SYNTHESIS-STUTTGART, 2004, (09): : 1509 - 1521
  • [4] Catalytic direct asymmetric Michael reactions: Taming naked aldehyde donors
    Betancort, JM
    Barbas, CF
    [J]. ORGANIC LETTERS, 2001, 3 (23) : 3737 - 3740
  • [5] Catalytic enantioselective direct Michael additions of ketones to alkylidene malonates
    Betancort, JM
    Sakthivel, K
    Thayumanavan, R
    Barbas, CF
    [J]. TETRAHEDRON LETTERS, 2001, 42 (27) : 4441 - 4444
  • [6] Protonated chiral catalysts: Versatile tools for asymmetric synthesis
    Bolm, C
    Rantanen, T
    Schiffers, I
    Zani, L
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (12) : 1758 - 1763
  • [7] A rapid 1H NMR assay for enantiomeric excess of α-substituted aldehydes
    Chi, Y
    Peelen, TJ
    Gellman, SH
    [J]. ORGANIC LETTERS, 2005, 7 (16) : 3469 - 3472
  • [8] Enantioselective Michael addition of nitromethane to α,β-enones catalyzed by chiral quaternary ammonium salts.: A simple synthesis of (R)-baclofen
    Corey, EJ
    Zhang, FY
    [J]. ORGANIC LETTERS, 2000, 2 (26) : 4257 - 4259
  • [9] In the golden age of organocatalysis
    Dalko, PI
    Moisan, L
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (39) : 5138 - 5175
  • [10] Enders D, 2002, SYNLETT, P26
12345