Catalytic asymmetric β-peroxidation of nitroalkenes

被引:46
作者
Russo, Alessio [1 ]
Lattanzi, Alessandra [1 ]
机构
[1] Univ Salerno, Dipartimento Chim, I-84084 Fisciano, Italy
关键词
asymmetric catalysis; Michael addition; nitroalkenes; organocatalysis; peroxides;
D O I
10.1002/adsc.200800387
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The first example of an asymmetric P-peroxidation of nitroalkenes is disclosed. The reaction is promoted by catalytic loadings of a commercially available diaryl-2-pyrrolidinemethanol derivative and tert-butyl hydroperoxide as the oxidant. A synthetically useful class of peroxides is obtained in good yield and enantioselectivity (up to 84% ee).
引用
收藏
页码:1991 / 1995
页数:5
相关论文
共 69 条
  • [1] Stereoselective syntheses of protected β-hydroxy-α-amino acids using (arylthio)nitrooxiranes
    Adams, ZM
    Jackson, RFW
    Palmer, NJ
    Rami, HK
    Wythes, MJ
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (08): : 937 - 947
  • [2] Highly diastereoselective oxy-Michael additions of enantiopure δ-lactol anions to nitroalkenes:: Asymmetric synthesis of 1,2-amino alcohols
    Adderley, NJ
    Buchanan, DJ
    Dixon, DJ
    Lainé, DI
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (35) : 4241 - 4244
  • [3] 1,2-amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis
    Ager, DJ
    Prakash, I
    Schaad, DR
    [J]. CHEMICAL REVIEWS, 1996, 96 (02) : 835 - 875
  • [4] Organocatalytic asymmetric conjugate additions
    Almasi, Diana
    Alonso, Diego A.
    Najera, Carmen
    [J]. TETRAHEDRON-ASYMMETRY, 2007, 18 (03) : 299 - 365
  • [5] [Anonymous], 2000, CATALYTIC ASYMMETRIC
  • [6] ARANTES SF, 1999, J CHEM RES, P801
  • [7] ASHWELL MA, 1988, SYNTHESIS-STUTTGART, P229
  • [8] Asymmetric catalytic synthesis of enantiopure N-protected 1,2-amino alcohols
    Bartoli, G
    Bosco, M
    Carlone, A
    Locatelli, M
    Melchiorre, P
    Sambri, L
    [J]. ORGANIC LETTERS, 2004, 6 (22) : 3973 - 3975
  • [9] The synthesis of vicinal amino alcohols
    Bergmeier, SC
    [J]. TETRAHEDRON, 2000, 56 (17) : 2561 - 2576
  • [10] Berner OM, 2002, EUR J ORG CHEM, V2002, P1877