Synthesis of novel isoxazoline-fused cyclic β-amino esters by regio- and stereo-selective 1,3-dipolar cycloaddition

被引:31
|
作者
Nonn, Melinda [1 ]
Kiss, Lorand [1 ]
Forro, Eniko [1 ]
Mucsi, Zoltan [3 ]
Fueloep, Ferenc [1 ,2 ]
机构
[1] Univ Szeged, Inst Pharmaceut Chem, H-6720 Szeged, Hungary
[2] Univ Szeged, Hungarian Acad Sci, Res Grp Stereochem, H-6720 Szeged, Hungary
[3] Univ Szeged, Dept Chem Informat, H-6720 Szeged, Hungary
关键词
NITRILE OXIDES; CYCLOPENTANE DERIVATIVES; PEPTIDES; ACIDS; INHIBITORS; HOMOLOGS;
D O I
10.1016/j.tet.2011.04.005
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Isoxazoline-fused 2-aminocyclopentanecarboxylate derivatives were regio- and stereo-selectively synthesized by nitrile oxide 1,3-dipolar cycloaddition to cis- or trans-ethyl-2-aminocyclopent-3-ene-carboxylates. The compounds were prepared in enantiomerically pure form by enzymatic resolution of the racemic bicyclic beta-lactam. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4079 / 4085
页数:7
相关论文
共 50 条
  • [31] Regio- and diastereoselectivity of the 1,3-dipolar cycloaddition of α-aryl nitrone with methacrolein. A theoretical investigation
    Benchouk, Wafaa
    Mekelleche, Sidi Mohamed
    RSC ADVANCES, 2015, 5 (28) : 22126 - 22134
  • [32] Synthesis of New Spirooxindole-Fused Isoxazoline/Triazole and Isoxazoline/Isoxazole Derivatives from Three-Component 1,3-Dipolar Cycloaddition
    Sakly, Randa
    Edziri, Hayet
    Askri, Moheddine
    Knorr, Michael
    Louven, Kathrin
    Strohmann, Carsten
    Mastouri, Maha
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2017, 54 (06) : 3554 - 3564
  • [33] Regio- and Stereoselective Multicomponent Synthesis of Novel Chromeno-Annulated Pyrrolizine and Thiazolizine Scaffolds via 1,3-Dipolar Cycloaddition Reactions
    Karmakar, Rajiv
    Mukhopadhyay, Chhanda
    CHEMISTRYSELECT, 2018, 3 (30): : 8581 - 8586
  • [34] Copper-Catalyzed Regio- and Diastereoselective 1,3-Dipolar Cycloaddition Reactions of Glycine Imino Esters with 1-Propene-1,3-sultone
    Furuya, Shohei
    Kato, Shuma
    Kanemoto, Kazuya
    Fukuzawa, Shin-ichi
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (28) : 4561 - 4565
  • [35] Regio- and stereoselective synthesis of new spirooxindoles via 1,3-dipolar cycloaddition reaction: Anticancer and molecular docking studies
    Lofty, Gehad
    El Ashry, El Sayed H.
    Said, Mohamed M.
    El Tamany, El Sayed
    Aziza, Yasmine M. Abdel
    Al-Dhfyan, Abdullah
    Al-Majid, Abdullah M.
    Barakat, Assem
    JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY B-BIOLOGY, 2018, 180 : 98 - 108
  • [36] 1,3-Dipolar Cycloaddition of Azomethine Ylides to Aldehydes: Synthesis of anti α-Amino-β-Hydroxy Esters
    Danielsson, Jakob
    Toom, Lauri
    Somfai, Peter
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (03) : 607 - 613
  • [37] Synthesis of 3,4-fused cycloalkanopyrroles by 1,3-dipolar cycloaddition
    Kelly, James M.
    Leeper, Finian J.
    TETRAHEDRON LETTERS, 2012, 53 (07) : 819 - 821
  • [38] Highly selective 1,3-dipolar cycloaddition of a cyclic azomethine ylide to ethyltrifluorocrotonates
    Bégué, JP
    Bonnet-Delpon, D
    Chennoufi, A
    Ourévitch, M
    Ravikumar, KS
    Rock, MH
    JOURNAL OF FLUORINE CHEMISTRY, 2001, 107 (02) : 275 - 279
  • [39] Regio- and Stereo-Selective Isomerization of Borylated 1,3-Dienes Enabled by Selective Energy Transfer Catalysis
    Kweon, Byeongseok
    Blank, Lukas
    Soika, Julia
    Messara, Amelia
    Daniliuc, Constantin G.
    Gilmour, Ryan
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2024, 63 (22)
  • [40] Multi-component, 1,3-dipolar cycloaddition reactions for the chemo-, regio- and stereoselective synthesis of novel hybrid spiroheterocycles in ionic liquid
    Rajesh, Stephen Michael
    Bala, Balasubramainan Devi
    Perumal, Subbu
    TETRAHEDRON LETTERS, 2012, 53 (40) : 5367 - 5371