1,3-dipolar cycloadditions.: Part XII -: Selective cycloaddition route to 4-nitroisoxazolidine ring systems

被引:15
作者
Banerji, Avijit
Gupta, Maya
Biswas, Pizush Kanti
Prange, Thierry
Neuman, Alain
机构
[1] Univ Calcutta, Univ Coll Sci & Technol, Dept Chem, Ctr Adv Studies Nat Prod, Kolkata 700009, W Bengal, India
[2] Univ Paris 13, CNRS, UMR 7033, Lab Chem Structurale Biomol, F-93012 Bobigny, France
关键词
D O I
10.1002/jhet.5570440511
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Cycloadditions of C,N-diarylnitrones to beta-nitrostyrenes occurred to yield two diastereoisomeric cycloadducts, the 3,4-trans-4,5-trans substituted isoxazolidine derivatives being formed selectively as the major products. These were characterised by spectroscopic and X-ray data. Conformational studies were carried out by X-ray crystallography and Molecular Modelling.
引用
收藏
页码:1045 / 1049
页数:5
相关论文
共 16 条
  • [1] [Anonymous], 1988, NITRILE OXIDES NITRO
  • [2] Unexpected cycloadducts from 1,3-dipolar cycloaddition of 3,4-dehydromorpholine N-oxide to N-cinnamoyl piperidines-first report of the novel formation of 2:1 cycloadducts
    Banerji, A
    Bandyopadhyay, D
    Prangé, T
    Neuman, A
    [J]. TETRAHEDRON LETTERS, 2005, 46 (15) : 2619 - 2622
  • [3] BANERJI A, 1986, J SCI IND RES INDIA, V45, P355
  • [4] 1,3-dipolar cycloadditions:: Investigation of cycloadditions of C-aryl-N-(4-chlorophenyl) nitrones to N-cinnamoyl piperidines
    Banerji, Avijit
    Biswas, Pizush Kanti
    Bandyopadhyay, Debasish
    Gupta, Maya
    Prange, Thierry
    Neuman, Aain
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2007, 44 (01) : 137 - 143
  • [5] BLACK DSC, 1975, SYNTHESIS-STUTTGART, P205
  • [6] Grant G. H., 1995, COMPUTATIONAL CHEM
  • [7] HOUK KN, 1984, 1 3 DIPOLAR CYCOADDI, V3, P407
  • [8] Regio- and stereospecific [3+2] cycloaddition of an unusual nitrone derived from a N-hydroxy-2-pyridone with medium ring enones
    Irlapati, NR
    Baldwin, JE
    Adlington, RM
    Pritchard, GJ
    Cowley, AR
    [J]. TETRAHEDRON, 2005, 61 (07) : 1773 - 1784
  • [9] The diastereoselective synthesis of functionalised isoxazolidines using a Cope elimination/intramolecular nitrone cycloaddition strategy
    O'Neil, IA
    Ramos, VE
    Ellis, GL
    Cleator, E
    Chorlton, AP
    Tapolczay, DJ
    Kalindjian, SB
    [J]. TETRAHEDRON LETTERS, 2004, 45 (18) : 3659 - 3661
  • [10] Evaluation of chiral bidentate ligand-metal complexes in asymmetric 1,3-dipolar cycloaddition reaction of nitrones with 3-alkenoyl-2-oxazolidinones
    Saito, T
    Yamada, T
    Miyazaki, S
    Otani, T
    [J]. TETRAHEDRON LETTERS, 2004, 45 (52) : 9581 - 9584