An Improved Protocol for Regioselective Ring-Opening of Sulfonyl Aziridines with Iodine Promoted by PPh3

被引:2
|
作者
Zhang, Jinfeng [1 ]
Meng, Lingguo [1 ]
Li, Chuntao [1 ]
Xiao, Guoyuan [1 ]
机构
[1] Huaibei Normal Univ, Dept Chem, Huaibei 235000, Anhui, Peoples R China
关键词
sulfonyl aziridines; iodine; ring-opening; -iodo amines; PPh3; CARBON BOND-CLEAVAGE; TETRABUTYLAMMONIUM HALIDES; N-TOSYLAZIRIDINES; BETA-LACTAMS; EPOXIDES; CYCLOADDITION; EXPANSION; WATER; ISOMERIZATION; REACTIVITY;
D O I
10.1002/cjoc.201300625
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new route to synthesize -iodo amines from sulfonyl aziridines and iodine was developed in the presence of PPh3. This ring-opening reaction was an efficient and simple process to give -iodo amines in excellent yields with high chemoselectivity.
引用
收藏
页码:1508 / 1512
页数:5
相关论文
共 50 条
  • [1] Unexpected highly efficient ring-opening of aziridines or epoxides with iodine promoted by thiophenol
    Wu, Jie
    Sun, Xiaoyu
    Sun, Wei
    Ye, Shengqing
    SYNLETT, 2006, (15) : 2489 - 2491
  • [2] A practical regioselective ring-opening of activated aziridines with organoalanes
    Bertolini, Ferruccio
    Woodward, Simon
    Crotti, Stefano
    Pineschi, Mauro
    TETRAHEDRON LETTERS, 2009, 50 (31) : 4515 - 4518
  • [3] Regioselective ring-opening of aziridines with thiophenol in the presence of β-cyclodextrin in water
    Reddy, MS
    Narender, M
    Rao, KR
    SYNLETT, 2005, (03) : 489 - 490
  • [4] Synthesis of (+)-Lycoricidine by the Application of Oxidative and Regioselective Ring-Opening of Aziridines
    Yadav, J. S.
    Satheesh, G.
    Murthy, Changalvala V. S. R.
    ORGANIC LETTERS, 2010, 12 (11) : 2544 - 2547
  • [5] Indium trichloride promoted regioselective ring opening of aziridines with TMS azide
    Yadav, JS
    Reddy, BVS
    Kumar, GM
    Murthy, CVSR
    SYNTHETIC COMMUNICATIONS, 2002, 32 (12) : 1797 - 1802
  • [6] Regioselective ring-opening of aziridines with potassium thiocyanate in the presence of β-cyclodextrin in water
    Reddy, MS
    Narender, M
    Nageswar, YVD
    Rao, KR
    TETRAHEDRON LETTERS, 2005, 46 (38) : 6437 - 6439
  • [7] Regioselective Ring-Opening Nucleophilic Addition of Aziridines through Photoredox Catalyst
    Sun, Hongnan
    Yang, Chao
    Lin, Run
    Xia, Wujiong
    ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (13) : 2775 - 2780
  • [8] RING-OPENING POLYMERIZATION OF [2.2] CYCLOPHANES PROMOTED BY IODINE
    GLATZHOFER, DT
    GUERRERO, DJ
    JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 1994, 32 (05) : 979 - 982
  • [9] Efficient ring-opening reaction of epoxides and aziridines promoted by tributylphosphine in water
    Fan, RH
    Hou, XL
    JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (03): : 726 - 730
  • [10] A PRACTICAL ALTERNATIVE TO SULFONYL ACTIVATION OF AZIRIDINES - RING-OPENING OF N-DIPHENYLPHOSPHINOYL AZIRIDINES BY CARBON NUCLEOPHILES
    OSBORN, HMI
    SWEENEY, JB
    HOWSON, W
    TETRAHEDRON LETTERS, 1994, 35 (17) : 2739 - 2742