Enantioselective radical addition reactions to imines using binaphthol-derived chiral N-triflyl phosphoramides

被引：43
|
作者：
Lee, Sunggi [1 ]
Kim, Sunggak [1 ]
机构：
[1] Korea Adv Inst Sci & Technol, Sch Mol Sci BK 21, Dept Chem, Taejon 305701, South Korea
来源：
TETRAHEDRON LETTERS | 2009年 / 50卷 / 26期
关键词：
Radical; Chiral Bronsted acid; Imine; Asymmetric; Catalytic; BRONSTED ACID CATALYST; TRANSFER HYDROGENATION; ALKYLATION; INDOLES;
D O I：
10.1016/j.tetlet.2009.02.136
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Binaphthol-derived chiral phosphoric acid catalysts were applied to enantioselective radical addition reactions of imines and provided chiral amines with good enantioselectivities (73-84% ee). Furthermore,, the enantioselectivities were not affected by either electronic properties of phenyl imines or radical precursors. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3345 / 3348
页数：4
相关论文
共 50 条
  • [1] Enantioselective Cycloaddition Reactions Catalyzed by BINOL-Derived Phosphoric Acids and N-Triflyl Phosphoramides: Recent Advances
    Held, Felix E.
    Grau, Dominik
    Tsogoeva, Svetlana B.
    MOLECULES, 2015, 20 (09) : 16103 - 16126
  • [2] Design and Synthesis of Chiral Binaphthol-Derived Bisphosphoric Acids and Their Application in the Catalytic Enantioselective Hydrogenation of Quinolines
    Wang, Pei
    Jia, Yan-E
    Zhao, Jia-Zhen
    Zhao, Dan
    Yuan, Rui
    Da, Chao-Shan
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 4 (05) : 430 - 433
  • [3] Asymmetric intramolecular oxa-Michael addition of activated α,β-unsaturated ketones by chiral N-triflyl phosphoramide
    FENG Zhen
    Science Bulletin, 2010, (17) : 1723 - 1725
  • [4] Asymmetric Friedel-Crafts reactions with fluoral catalyzed by chiral binaphthol-derived titanium catalysts
    Ishii, Akihiro
    Mikami, Koichi
    ACS Symposium Series, 746 : 60 - 71
  • [5] Asymmetric Friedel-Crafts reactions with fluoral catalyzed by chiral binaphthol-derived titanium catalysts
    Ishii, A
    Mikami, K
    ASYMMETRIC FLUOROORGANIC CHEMISTRY: SYNTHESIS, APPLICATIONS, AND FUTURE DIRECTIONS, 2000, 746 : 60 - 71
  • [6] Binaphthol-derived phosphoric acid as a versatile catalyst for enantioselective carbon-carbon bond forming reactions
    Terada, Masahiro
    CHEMICAL COMMUNICATIONS, 2008, (35) : 4097 - 4112
  • [7] ENANTIOSELECTIVE AND DIASTEREOSELECTIVE CATALYSIS OF ADDITION-REACTION OF ALLYLIC SILANES AND STANNANES TO GLYOXYLATES BY BINAPHTHOL-DERIVED TITANIUM COMPLEX
    AOKI, S
    MIKAMI, K
    TERADA, M
    NAKAI, T
    TETRAHEDRON, 1993, 49 (09) : 1783 - 1792
  • [8] Asymmetric intramolecular oxa-Michael addition of activated α,β-unsaturated ketones by chiral N-triflyl phosphoramide
    Feng Zhen
    Zeng Mi
    Xu QingLong
    You ShuLi
    CHINESE SCIENCE BULLETIN, 2010, 55 (17): : 1723 - 1725
  • [9] Enantioselective synthesis of fluorene derivatives by chiral N-triflyl phosphoramide catalyzed double Friedel-Crafts alkylation reaction
    Wang, Shou-Guo
    Han, Long
    Zeng, Mi
    Sun, Feng-Lai
    Zhang, Wei
    You, Shu-Li
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (16) : 3202 - 3209
  • [10] Asymmetric catalysis of carbonyl-ene and aldol reactions with fluoral by chiral binaphthol-derived titanium complex
    Mikami, K
    Yajima, T
    Takasaki, T
    Matsukawa, S
    Terada, M
    Uchimaru, T
    Maruta, M
    TETRAHEDRON, 1996, 52 (01) : 85 - 98
12345