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
  • [21] PPh3/halogenating agent-mediated highly efficient ring opening of activated and non-activated aziridines
    Kumar, Manoj
    Pandey, Sanjay K.
    Gandhi, Shikha
    Singh, Vinod K.
    TETRAHEDRON LETTERS, 2009, 50 (03) : 363 - 365
  • [22] Regioselective Ring-Opening Reaction of Cyclopropene Carboxylate Promoted by N-Bromosuccinimide
    Xu, Lulu
    Ye, Qianwen
    Cheng, Dongping
    Li, Xiaonian
    Xu, Xiaoliang
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2019, 39 (09) : 2645 - 2649
  • [23] Electron transfer promoted regioselective ring-opening reaction of cyclopropyl silyl ethers
    Hasegawa, Eietsu
    Yamaguchi, Naoto
    Muraoka, Hiroyasu
    Tsuchida, Hiroyuki
    ORGANIC LETTERS, 2007, 9 (15) : 2811 - 2814
  • [24] Highly regioselective ring-opening of aziridines with arenesulfinates on water: a facile access to β-amino/vinyl sulfones
    Chawla, Ruchi
    Singh, Atul K.
    Yadav, Lal Dhar S.
    TETRAHEDRON, 2013, 69 (06) : 1720 - 1724
  • [25] REGIOSELECTIVE CYANIDE RING-OPENING OF C-2 SYMMETRICAL BIS-AZIRIDINES BY CYANIDE
    FITREMANN, J
    DUREAULT, A
    DEPEZAY, JC
    SYNLETT, 1995, (03) : 235 - 237
  • [26] Synthesis of diverse β-(nitrooxy)-substituted amines by regioselective ring-opening of aziridines under neat conditions
    Samanta, Satyajit
    Chatterjee, Rana
    Mahato, Sachinta
    Hajra, Alakananda
    Santra, Sougata
    Zyryanov, Grigory V.
    Majee, Adinath
    SYNTHETIC COMMUNICATIONS, 2018, 48 (14) : 1857 - 1866
  • [27] Organocatalysis by an aprotic imidazolium zwitterion: regioselective ring-opening of aziridines and applicable to gram scale synthesis
    Ghosal, Nirnita Chakraborty
    Santra, Sougata
    Das, Sudarshan
    Hajra, Alakananda
    Zyryanov, Grigory V.
    Majee, Adinath
    GREEN CHEMISTRY, 2016, 18 (02) : 565 - 574
  • [28] A rapid regioselective ring-opening of aziridines with potassium thiocyanate using ammonium-12-molybdophosphate
    Das, Biswanath
    Reddy, V. Saidi
    Ramu, R.
    Kumar, D. Nandan
    CATALYSIS COMMUNICATIONS, 2006, 7 (12) : 997 - 999
  • [29] Tf2O-Promoted Regioselective Heteronucleophilic Ring-Opening Approaches of Tetrahydrofuran
    Bhat, Mohammad Yaqoob
    Padder, Ashiq Hussain
    Gupta, Raman
    Ahmed, Qazi Naveed
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (20): : 14323 - 14338
  • [30] A Mild and Regioselective Ring-Opening of Aziridines with Acid Anhydride Using TBD or PS-TBD as a Catalyst
    Matsukawa, Satoru
    Mouri, Yasutaka
    MOLECULES, 2015, 20 (10): : 18482 - 18495