An iterative approach to novel polyamines via nucleophilic ring-opening of aziridinium ions with β-amino alcohols

被引:13
|
作者
McKay, C [1 ]
Wilson, RJ [1 ]
Rayner, CM [1 ]
机构
[1] Univ Leeds, Dept Chem, Leeds LS2 9JT, W Yorkshire, England
关键词
D O I
10.1039/b401447b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An iterative procedure for the synthesis of a novel class of synthetic polyamines has been developed, utilising the regioselective ring-opening of aziridinium ion intermediates; facile N-allyl deprotection of intermediate polyamines allows the rapid construction of high molecular weight, stereochemically defined compounds in a convergent manner.
引用
收藏
页码:1080 / 1081
页数:2
相关论文
共 50 条
  • [21] Insight into the Regioselectivity of Nucleophilic Ring-Opening of Azetidinium Ions Containing Quaternary Carbon Atoms
    Drouillat, Bruno
    Wright, Karen
    David, Olivier
    Couty, Francois
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (30) : 6005 - 6012
  • [22] β3-amino acids by nucleophilic ring-opening of N-nosyl aziridines
    Farràs, J
    Ginesta, X
    Sutton, PW
    Taltavull, J
    Egeler, F
    Romea, P
    Urpí, F
    Vilarrasa, J
    TETRAHEDRON, 2001, 57 (36) : 7665 - 7674
  • [23] Nucleophilic Ring-Opening of Epoxide and Aziridine Acetates for the Stereodivergent Synthesis of β-Hydroxy and β-Amino γ-Lactams
    Bisol, Tula B.
    Bortoluzzi, Adailton J.
    Sa, Marcus M.
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (03): : 948 - 962
  • [24] Cationic ring-opening polymerization of N-benzylaziridines to polyamines via organic boron
    Gu, Ge-Ge
    Yue, Tian-Jun
    Ren, Wei-min
    CHEMICAL COMMUNICATIONS, 2023, 59 (20) : 2982 - 2985
  • [25] Asymmetric Organocatalytic Efficiency of Synthesized Chiral β-Amino Alcohols in Ring-Opening of Glycidol with Phenols
    Aral, Tarik
    Karakaplan, Mehmet
    Hosgoren, Halil
    CATALYSIS LETTERS, 2012, 142 (06) : 794 - 802
  • [26] Synthesis of β-amino alcohols using the tandem reduction and ring-opening reaction of nitroarenes and epoxides
    Shi, Chongyang
    Ren, Cheng
    Zhang, Erlei
    Jin, Huile
    Yu, Xiaochun
    Wang, Shun
    TETRAHEDRON, 2016, 72 (27-28) : 3839 - 3843
  • [27] Stereoselective ring-opening of N-tert-butanesulfinylaziridines:: Access to acetylenic α-amino alcohols
    Palais, Laetitia
    Chemla, Fabrice
    Ferreira, Franck
    SYNLETT, 2006, (07) : 1039 - 1042
  • [28] Asymmetric Organocatalytic Efficiency of Synthesized Chiral β-Amino Alcohols in Ring-Opening of Glycidol with Phenols
    Tarik Aral
    Mehmet Karakaplan
    Halil Hoşgören
    Catalysis Letters, 2012, 142 : 794 - 802
  • [29] Selective ring-opening of nonactivated amino aziridines by thiols and unusual nucleophilic substitution of a dibenzylamino group
    Concellón, JM
    Bernad, PL
    Suárez, JR
    JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (23): : 9411 - 9416
  • [30] The asymmetric synthesis of (S,S)-methylphenidate hydrochloride via ring-opening of an enantiopure aziridinium intermediate with phenylmagnesium bromide
    Davies, Stephen G.
    Fletcher, Ai M.
    Peters, Matthew E.
    Roberts, Paul M.
    Thomson, James E.
    TETRAHEDRON, 2019, 75 (49)