CYCLOADDITION REACTION OF 2,2-DIMETHYL-3,4-DIHYDRO-2H-PYRROLE N-OXIDE WITH UNSATURATED SUGAR LACTONES AND ESTERS

被引:0
|
作者
BASKARAN, S [1 ]
TRIVEDI, GK [1 ]
机构
[1] INDIAN INST TECHNOL,DEPT CHEM,BOMBAY 400076,MAHARASHTRA,INDIA
来源
关键词
D O I
暂无
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Intermolecular asymmetric 1,3-dipolar cycloaddition of 2,2-dimethyl-3,4-dihydro-2H-pyrrole N-oxide with optically active alpha,beta-unsaturated esters 1,2 gave diastereoisomers 8-10 and with sugar lactones (3 and 6) gave cycloadducts stereo-selectively (11 and 12); the stereochemistry of the products was established using high-field NMR techniques.
引用
收藏
页码:308 / 309
页数:2
相关论文
共 50 条
  • [41] STRUCTURES OF SULFUR ANALOGS OF PRECOCENES .2. 6,7-DIMETHOXY-2,2-DIMETHYL-3,4-EPOXY-3,4-DIHYDRO-2H-1-BENZOTHIOPYRAN 1,1-DIOXIDE
    DESIMONE, CA
    ZUKERMANSCHPECTOR, J
    CASTELLANO, EE
    TERCIO, J
    FERREIRA, B
    CATANI, V
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1989, 45 : 961 - 962
  • [42] SYNTHESIS OF (S)-3,4-DIHYDRO-2-PIVALOYLOXYMETHYL-2H-PYRROLE 1-OXIDE
    DEMARCH, P
    FIGUEREDO, M
    FONT, J
    GALLAGHER, T
    MILAN, S
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (20) : 2097 - 2098
  • [43] 3,4-Dihydro-2H-pyrrole-2-carbonitriles: Useful Intermediates in the Synthesis of Fused Pyrroles and 2,2′-Bipyrroles
    Nebe, Marco M.
    Kucukdisli, Murat
    Opatz, Till
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (10): : 4112 - 4121
  • [44] Synthesis of 6-(2,2-dimethyl-3,4-dihydro-3-oxo1,4(2H)-benzoxazin-7-yl)pyridazin-3-ones
    Moussavi, Z
    Lebegue, N
    Carato, P
    Yous, S
    Berthelot, P
    ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2004, 36 (03) : 292 - 296
  • [45] Efficient synthesis of (S)-3,4-dihydro-2-pivaloyloxymethyl-2H-pyrrole 1-oxide
    Busqué, F
    de March, P
    Figueredo, M
    Font, J
    Gallagher, T
    Milán, S
    TETRAHEDRON-ASYMMETRY, 2002, 13 (04) : 437 - 445
  • [46] 2-(2-Ethynyl-1-aziranyl)-3,4-dihydro-2H-pyrrole: a one-pot assembly from isopropyl phenyl ketoxime and acetylene during the synthesis of 3H-pyrrole
    Shabalin, Dmitrii A.
    Glotova, Tatyana E.
    Ushakov, Igor A.
    Dvorko, Marina Yu.
    Vashchenko, Alexander V.
    Smirnov, Vladimir I.
    Schmidt, Elena Yu.
    Mikhaleva, Al'bina I.
    Trofimov, Boris A.
    MENDELEEV COMMUNICATIONS, 2014, 24 (06) : 368 - 369
  • [47] An investigation of the molecular mechanism, chemoselectivity and regioselectivity of cycloaddition reaction between acetonitrile N-Oxide and 2,5-dimethyl-2H-[1,2,3]diazaphosphole: a MEDT study
    Zeroual, Abdellah
    Rios-Gutierrez, Mar
    Salah, Mohammed
    El Abdallaoui, Habib El Alaoui
    Ramon Domingo, Luis
    JOURNAL OF CHEMICAL SCIENCES, 2019, 131 (08)
  • [48] An investigation of the molecular mechanism, chemoselectivity and regioselectivity of cycloaddition reaction between acetonitrile N-Oxide and 2,5-dimethyl-2H-[1,2,3]diazaphosphole: a MEDT study
    Abdellah Zeroual
    Mar Ríos-Gutiérrez
    Mohammed Salah
    Habib El Alaoui El Abdallaoui
    Luis Ramon Domingo
    Journal of Chemical Sciences, 2019, 131
  • [49] 5-ISOPROPYLIDEN-1,2-OXATHIOLE 2-OXIDE BY PHOTOISOMERIZATION OF 2,2-DIMETHYL-3(2H)-THIOPHENONE 1-OXIDE
    KOWALEWSKI, R
    MARGARETHA, P
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1988, 27 (10): : 1374 - 1375
  • [50] 2-Ethoxycarbonyl-2-methyl-3,4-dihydro-2H-pyrrole-1-oxide:: evaluation of the spin trapping properties
    Olive, G
    Mercier, A
    Le Moigne, F
    Rockenbauer, A
    Tordo, P
    FREE RADICAL BIOLOGY AND MEDICINE, 2000, 28 (03) : 403 - 408