Copper(II)-Bis(oxazoline) catalyzed asymmetric Diels-Alder reaction with α'-arylsulfonyl enones as dienophiles

被引:16
|
作者
Barroso, Santiago [2 ]
Blay, Gonzalo [2 ]
Al-Midfa, Lina [2 ]
Munoz, M. Carmen [1 ]
Pedro, Jose R. [2 ]
机构
[1] Univ Politecn Valencia, Dept Fis Aplicada, E-46071 Valencia, Spain
[2] Univ Valencia, Dept Quim Organ, Fac Quim, E-46100 Burjassot, Valencia, Spain
来源
JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 16期
关键词
D O I
10.1021/jo8009227
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] alpha'-Arylsulfonyl enones are efficient bidentate dienophiles for the Cu(II)-bis(oxazoline) catalyzed enantioselective Diels-Alder reaction with a number of dienes, affording the corresponding products with good to high enantiomeric excesses. The resulting products can be alkylated and the sulfone removed, so alpha'-arylsulfonyl enones can be regarded as surrogates of simple monodentate enones, which are poor dienophiles with this catalytic system.
引用
收藏
页码:6389 / 6392
页数:4
相关论文
共 50 条
  • [1] Bis(oxazoline) copper(II) catalysis of the Diels-Alder reaction
    Franklin, Edward G.
    DeChancie, Jason
    Evanseck, Jeffrey D.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 231
  • [2] Asymmetric copper-catalyzed Diels-Alder reaction revisited: control of the structure of bis(oxazoline) ligands
    Le Maux, Paul
    Dorcet, Vincent
    Simonneaux, Gerard
    TETRAHEDRON, 2013, 69 (38) : 8291 - 8298
  • [3] Catalytic asymmetric hetero Diels-Alder reactions of N-sulfinyl dienophiles with chiral bis(oxazoline)copper(II) and -zinc(II) triflates
    Endeshaw, Molla Mellese
    Bayer, Annette
    Hansen, Lars K.
    Gautun, Odd R.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (23) : 5249 - 5259
  • [4] BIS(OXAZOLINE)COPPER(II) COMPLEXES AS CHIRAL CATALYSTS FOR THE ENANTIOSELECTIVE DIELS-ALDER REACTION
    EVANS, DA
    MILLER, SJ
    LECTKA, T
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (14) : 6460 - 6461
  • [5] Counter-ion effects of bis(oxazoline) copper(II) catalyzed Diels-Alder reactions
    Franklin, Edward G.
    DeChancie, Jason
    Evanseck, Jeffrey D.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 231
  • [6] ASYMMETRIC DIELS-ALDER REACTION - APPLICATIONS OF CHIRAL DIENOPHILES
    MASAMUNE, S
    REED, LA
    DAVIS, JT
    CHOY, W
    JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (23): : 4441 - 4444
  • [7] ASYMMETRIC DIELS-ALDER REACTION - DESIGN OF CHIRAL DIENOPHILES
    CHOY, W
    REED, LA
    MASAMUNE, S
    JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (07): : 1137 - 1139
  • [9] Asymmetric Diels-Alder reactions on supported bis(oxazoline) catalysts
    Wang Hong
    Liu Jian
    Liu Peng
    Yang Qihua
    Xiao Jianliang
    Li Can
    CHINESE JOURNAL OF CATALYSIS, 2006, 27 (11) : 946 - 948
  • [10] Asymmetric Diels-Alder reaction catalyzed by novel chiral dibenzo [a,c]cycloheptadiene bis(oxazoline) metal complexes
    Fu, B
    Du, DM
    CHINESE JOURNAL OF CHEMISTRY, 2003, 21 (06) : 597 - 599