Organocatalytic Enantioselective Morita-Baylis-Hillman Reaction of Maleimides with Isatins

被引:20
|
作者
Chauhan, Pankaj [1 ]
Chimni, Swapandeep Singh [1 ]
机构
[1] Guru Nanak Dev Univ, Dept Chem, UGC Sponsored Ctr Adv Studies Chem, Amritsar 143005, Punjab, India
关键词
cinchona alkaloids; maleimides; Morita-Baylis-Hillman reaction; organocatalysis; oxindoles; CATALYTIC ASYMMETRIC-SYNTHESIS; VICINAL QUATERNARY; ALDOL REACTION; CONSTRUCTION; FACILE; 3-HYDROXYOXINDOLE; DERIVATIVES; INDOLES; BEARING; CARBON;
D O I
10.1002/ajoc.201300093
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An enantioselective Morita-Baylis-Hillman reaction of maleimides with isatin derivatives has been developed. beta-Isocupreidine catalyzes the formation of enantiomerically enriched 3-substituted 3-hydroxyoxindole derivatives in up to 96% yield and enantioselectivity of over 99% ee can be achieved under mild reaction conditions.
引用
收藏
页码:586 / 592
页数:7
相关论文
共 50 条
  • [41] Organocatalytic asymmetric allylic alkylation of sulfonylimidates with Morita-Baylis-Hillman carbonates
    PENG JingCUI HaiLei CHEN YingChun Key Laboratory of DrugTargeting and Drug Delivery SystemMinistry of Education
    Department of Medicinal ChemistryWest China School of PharmacySichuan UniversityChengdu China
    Science China(Chemistry), 2011, 54 (01) : 81 - 86
  • [42] Organocatalytic asymmetric allylic alkylation of oxindoles with Morita-Baylis-Hillman carbonates
    Jiang, Kun
    Peng, Jing
    Cui, Hai-Lei
    Chen, Ying-Chun
    CHEMICAL COMMUNICATIONS, 2009, (26) : 3955 - 3957
  • [43] Organocatalytic asymmetric allylic alkylation of sulfonylimidates with Morita-Baylis-Hillman carbonates
    PENG Jing
    Department of Medicinal Chemistry
    Science China(Chemistry), 2011, (01) : 81 - 86
  • [44] Toward the development of an asymmetric Morita-Baylis-Hillman reaction
    Lin, YM
    Boucau, J
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 230 : U3441 - U3441
  • [45] Ionic Thiourea Organocatalysis of the Morita-Baylis-Hillman Reaction
    McGrath, Trevor
    Robertson, Katherine N.
    Masuda, Jason D.
    Clyburne, Jason A. C.
    Singer, Robert D.
    AUSTRALIAN JOURNAL OF CHEMISTRY, 2016, 69 (07) : 759 - 762
  • [46] Asymmetric Morita-Baylis-Hillman reaction of chiral glyoxylates
    Bauer, T
    Tarasiuk, J
    TETRAHEDRON-ASYMMETRY, 2001, 12 (12) : 1741 - 1745
  • [47] Morita-Baylis-Hillman reaction of a chiral aziridine aldehyde
    Lee, Jaedeok
    Singh, Deepak
    Ha, Hyun-Joon
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (43) : 8048 - 8055
  • [48] Morita-Baylis-Hillman reaction of acrylamide with isatin derivatives
    Singh, Radhey M.
    Bharadwaj, Kishor Chandra
    Tiwari, Dharmendra Kumar
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2014, 10 : 2975 - 2980
  • [49] Chiral phosphine-squaramides as enantioselective catalysts for the intramolecular Morita-Baylis-Hillman reaction
    Song, Hong-Liang
    Yuan, Kui
    Wu, Xin-Yan
    CHEMICAL COMMUNICATIONS, 2011, 47 (03) : 1012 - 1014
  • [50] Highly enantioselective aza Morita-Baylis-Hillman reaction catalyzed by bifunctional β-isocupreidine derivatives
    Abermil, Nacim
    Masson, Geraldine
    Zhu, Jieping
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (38) : 12596 - +