Synthesis of chiral 1-(2-aminoalkyl)aziridines via a self-opening reaction of aziridine

被引:4
作者
Pieczonka, Adam M. [1 ]
Misztal, Ewelina [1 ]
Rachwalski, Michal [1 ]
Lesniak, Stanislaw [1 ]
机构
[1] Univ Lodz, Dept Organ & Appl Chem, Tamka 12, PL-91403 Lodz, Poland
关键词
Aziridine; diamine; aminoalkylaziridine; ring-opening of aziridine; ASYMMETRIC ADDITIONS; COMPLEXES; DIAMINES; ALCOHOLS; LIGAND; ALDEHYDES;
D O I
10.3998/ark.5550190.p009.741
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel approach to the synthesis of optically pure 1-(2-aminoalkyl)aziridines via a nucleophilic ring-opening reaction of aziridine is presented. The reaction takes place under mild conditions in the presence of ZnBr2 with moderate chemical yields. The formation of 1-(2-aminoalkyl)aziridines, starting from optically pure NH-aziridines, occurs selectively, leading to a single diastereoisomer.
引用
收藏
页码:223 / 234
页数:12
相关论文
共 34 条
  • [1] Synthesis and biological evaluation of aziridine-containing analogs of phytosphingosine
    Ballereau, Stephanie
    Andrieu-Abadie, Nathalie
    Saffon, Nathalie
    Genisson, Yves
    [J]. TETRAHEDRON, 2011, 67 (14) : 2570 - 2578
  • [2] STEREOSPECIFIC REDUCTION OF ZINC AZIRIDINYL-KETONE-BROMIDE COMPLEXES
    BARTNIK, R
    LESNIAK, S
    LAURENT, A
    [J]. TETRAHEDRON LETTERS, 1981, 22 (48) : 4811 - 4812
  • [3] Bartnik R., 1982, J CHEM RES, V287, P2701
  • [4] Reactions of Cu(I)Br with aziridine derivatives. Synthesis, characterization and crystal structures of monomeric, dimeric and hexameric aziridine (= az) complexes of the formal type [CuBr(az)2]n (n=1, 2) and [CuBr(az)]6
    Bobka, Roman
    Roedel, J. Nicolas
    Wirth, Stefan
    Lorenz, Ingo-Peter
    [J]. DALTON TRANSACTIONS, 2010, 39 (42) : 10142 - 10147
  • [5] Botuha C, 2011, HETEROCYCLES IN NATURAL PRODUCT SYNTHESIS, P3
  • [6] Synthesis, structural characterization, antimicrobial and cytotoxic effects of aziridine, 2-aminoethylaziridine and azirine complexes of copper(II) and palladium(II)
    Budzisz, E.
    Bobka, R.
    Hauss, A.
    Roedel, J. N.
    Wirth, S.
    Lorenz, I. -P.
    Rozalska, B.
    Wieckowska-Szakiel, M.
    Krajewska, U.
    Rozalski, M.
    [J]. DALTON TRANSACTIONS, 2012, 41 (19) : 5925 - 5933
  • [7] Lewis acid-catalyzed dimerization of N-unprotected aziridines
    Caiazzo, A
    Dalili, S
    Yudin, AK
    [J]. SYNLETT, 2003, (14) : 2198 - 2202
  • [8] The first synthesis of enantiopure α-amino ketimines and amino aziridines
    Concellón, JM
    Bernad, PL
    Riego, E
    García-Granda, S
    Forcén-Acebal, A
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (08) : 2764 - 2768
  • [9] Addition Reactions of Chloro- or Iodomethyllithium to Imines. Synthesis of Enantiopure Aziridines and β-Chloroamines
    Concellon, Jose M.
    Rodriguez-Solla, Humberto
    Bernad, Pablo L.
    Simal, Carmen
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (06) : 2452 - 2459
  • [10] FAURE R, 1981, CRYST STRUCT COMMUN, V10, P515