Amine-promoted, organocatalytic aziridination of enones

被引:83
作者
Armstrong, Alan [1 ]
Baxter, Carl A.
Lamont, Scott G.
Pape, Andrew R.
Wincewicz, Richard
机构
[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England
[2] AstraZeneca, Macclesfield SK10 4TG, Cheshire, England
基金
英国工程与自然科学研究理事会;
关键词
D O I
10.1021/ol062852v
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel method is presented using N-N ylides (prepared by in situ amination of a tertiary amine) for the aziridination of a range of enone systems. The amine may be used sub-stoichiometrically, and promising levels of enantioselectivity are observed with quinine as promoter.
引用
收藏
页码:351 / 353
页数:3
相关论文
共 23 条
  • [1] Asymmetric synthesis of N-aryl aziridines
    Aires-de-Sousa, J
    Prabhakar, S
    Lobo, AM
    Rosa, AM
    Gomes, MJS
    Corvo, MC
    Williams, DJ
    White, AJP
    [J]. TETRAHEDRON-ASYMMETRY, 2002, 12 (24) : 3349 - 3365
  • [2] A new enantioselective synthesis of N-arylaziridines by phase-transfer catalysis
    AiresdeSousa, J
    Lobo, AM
    Prabhakar, S
    [J]. TETRAHEDRON LETTERS, 1996, 37 (18) : 3183 - 3186
  • [3] N-amino-N-methylmorpholinium salts: Highly active aziridination reagents for chalcones
    Armstrong, Alan
    Carbery, David R.
    Lamont, Scott G.
    Pape, Andrew R.
    Wincewicz, Richard
    [J]. SYNLETT, 2006, (15) : 2504 - 2506
  • [4] COLVIN EW, 1982, TETRAHEDRON LETT, V23, P3835, DOI 10.1016/S0040-4039(00)87720-5
  • [5] In the golden age of organocatalysis
    Dalko, PI
    Moisan, L
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (39) : 5138 - 5175
  • [6] Nucleophilic chiral amines as catalysts in asymmetric synthesis
    France, S
    Guerin, DJ
    Miller, SJ
    Lectka, T
    [J]. CHEMICAL REVIEWS, 2003, 103 (08) : 2985 - 3012
  • [7] Recent advances in metal-mediated carbon-nitrogen bond formation reactions: Aziridination and amidation
    Halfen, JA
    [J]. CURRENT ORGANIC CHEMISTRY, 2005, 9 (07) : 657 - 669
  • [8] Nucleophilic ring opening of aziridines
    Hu, XE
    [J]. TETRAHEDRON, 2004, 60 (12) : 2701 - 2743
  • [9] IKEDA I, 1980, SYNTHESIS-STUTTGART, P650
  • [10] Jin SL, 2002, TETRAHEDRON, V58, P8321