Lewis base catalyzed ring opening of aziridines with silylated nucleophiles

被引:81
|
作者
Minakata, S [1 ]
Okada, Y [1 ]
Oderaotoshi, Y [1 ]
Komatsu, M [1 ]
机构
[1] Osaka Univ, Grad Sch Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan
关键词
D O I
10.1021/ol051186f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The ring opening of N-tosylaziridines with trimethylsilylated nucleophiles, catalyzed by N,N,N'N'-tetramethylethylenediamine, led to the production of beta-functionalized sulfonamides in good to excellent yields with high regioselectivity.
引用
收藏
页码:3509 / 3512
页数:4
相关论文
共 50 条
  • [41] Orthogonal Lewis acids: Catalyzed ring opening and rearrangement of acylaziridines
    Ferraris, D
    Drury, WJ
    Cox, C
    Lectka, T
    JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (14): : 4568 - 4569
  • [42] Lewis Acid Catalyzed Highly Stereoselective Domino-Ring-Opening Cyclization of Activated Aziridines with Enolates: Synthesis of Functionalized Chiral γ-Lactams
    Ghorai, Manas K.
    Tiwari, Deo Prakash
    JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (18): : 6173 - 6181
  • [43] Regiodivergent Ring Opening of Chiral Aziridines
    Wu, Bin
    Parquette, Jon R.
    RajanBabu, T. V.
    SCIENCE, 2009, 326 (5960) : 1662 - 1662
  • [44] Catalytic, Enantioselective Ring Opening of Aziridines
    Schneider, Christoph
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (12) : 2082 - 2084
  • [45] Regioselective Ring Opening of N-H-Aziridines with Sulfur Nucleophiles in Liquid SO2
    Luginina, Jevgenija
    Turks, Maris
    SYNLETT, 2017, 28 (08) : 939 - 943
  • [46] Nucleophilic ring opening reactions of aziridines
    Akhtar, Rabia
    Naqvi, Syed Ali Raza
    Zahoor, Ameer Fawad
    Saleem, Sameera
    MOLECULAR DIVERSITY, 2018, 22 (02) : 447 - 501
  • [47] Activation of aziridines: Nucleophilic ring opening
    Dangel, BD
    Polt, R
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1999, 217 : U79 - U79
  • [48] Unexplored Nucleophilic Ring Opening of Aziridines
    Maria Costero, Ana
    Gil, Salvador
    Parra, Margarita
    Rodriguez, Pablo
    MOLECULES, 2010, 15 (12): : 9135 - 9144
  • [49] Nucleophilic ring opening reactions of aziridines
    Rabia Akhtar
    Syed Ali Raza Naqvi
    Ameer Fawad Zahoor
    Sameera Saleem
    Molecular Diversity, 2018, 22 : 447 - 501
  • [50] Regioselective ring opening of phenyl aziridines
    Wong, Alexander
    Tarahomi, Justin
    Hart, Matthew
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 253