Enantioselective aziridination reaction of α,β-unsaturated aldehydes using an organocatalyst and tert-butyl N-arenesulfonyloxycarbamates

被引:66
作者
Arai, Hiromi [1 ]
Sugaya, Naomi [1 ]
Sasaki, Neri [1 ]
Makino, Kazuishi [1 ]
Lectard, Sylvain [1 ]
Hamada, Yasumasa [1 ]
机构
[1] Chiba Univ, Grad Sch Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan
关键词
ASYMMETRIC AZIRIDINATION; MOLECULES; AMINATION; PROLINE; OLEFINS; ETHERS;
D O I
10.1016/j.tetlet.2009.02.095
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An organocatalytic enantioselective aziridination reaction of alpha,beta-unsaturated aldehydes including aromatic substrates using N-arenesulfonyloxycarbamates in the presence of diphenylprolinol triethylsilyl ether and sodium carbonate or sodium acetate is described.
引用
收藏
页码:3329 / 3332
页数:4
相关论文
共 41 条
  • [1] Amine-promoted, organocatalytic aziridination of enones
    Armstrong, Alan
    Baxter, Carl A.
    Lamont, Scott G.
    Pape, Andrew R.
    Wincewicz, Richard
    [J]. ORGANIC LETTERS, 2007, 9 (02) : 351 - 353
  • [2] ENANTIOSPECIFIC PREPARATION OF [(2R, 6S)-ENDO]-5-AZA-1,10,10-TRIMETHYL-3-OXATRICYCLO[5.2.1.0(2,6)]DECAN-4-ONE BY A NITRENE-MEDIATED ROUTE FROM [(1S)-ENDO]-(-)-BORNEOL AND ITS UTILITY AS A CHIRAL AUXILIARY IN SOME ASYMMETRIC TRANSFORMATIONS
    BANKS, MR
    BLAKE, AJ
    CADOGAN, JIG
    DAWSON, IM
    GOSNEY, I
    GRANT, KJ
    GAUR, S
    HODGSON, PKG
    KNIGHT, KS
    SMITH, GW
    STEVENSON, DE
    [J]. TETRAHEDRON, 1992, 48 (37) : 7979 - 8006
  • [4] NEW METHODS FOR OXIDATION OF ALDEHYDES TO CARBOXYLIC ACIDS AND ESTERS
    COREY, EJ
    GILMAN, NW
    GANEM, BE
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (20) : 5616 - &
  • [5] Aziridines versus vinyl carbamates from the direct amination of electron-withdrawing group-substituted trifluoromethyl enoates
    Fioravanti, S
    Colantoni, D
    Pellacani, L
    Tardella, PA
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (08) : 3296 - 3298
  • [6] Synthesis of N-protected cyano aziridines
    Fioravanti, S
    Morreale, A
    Pellacani, L
    Tardella, PA
    [J]. SYNLETT, 2004, (06) : 1083 - 1085
  • [7] Aza-MIRC reactions of sulfonyl-activated hydroxycarbamates with α,β-difunctionalised acrylates
    Fioravanti, S
    Morreale, A
    Pellacani, L
    Tardella, PA
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (23) : 4549 - 4552
  • [8] Fioravanti S, 2001, SYNTHESIS-STUTTGART, P1975
  • [9] Recent advances in metal-mediated carbon-nitrogen bond formation reactions: Aziridination and amidation
    Halfen, JA
    [J]. CURRENT ORGANIC CHEMISTRY, 2005, 9 (07) : 657 - 669
  • [10] Total synthesis of halipeptin A, a potent anti-inflammatory cyclodepsipeptide from a marine sponge
    Hara, S
    Makino, K
    Hamada, Y
    [J]. TETRAHEDRON LETTERS, 2006, 47 (07) : 1081 - 1085