Enantiomeric resolution and determination of the absolute configuration of dibenzophosphole 5-oxides

被引：33
|
作者：
Durán, E
Gordo, E
Granell, J
Font-Bardía, M
Solans, X
Velasco, D
López-Calahorra, F
机构：
[1] Univ Barcelona, Dept Quim Organ, E-08028 Barcelona, Spain
[2] Univ Barcelona, Dept Quim Inorgan, E-08028 Barcelona, Spain
[3] Univ Barcelona, Dept Cristallog & Diposits Minerals, E-08028 Barcelona, Spain
来源：
TETRAHEDRON-ASYMMETRY | 2001年 / 12卷 / 14期
关键词：
D O I：
10.1016/S0957-4166(01)00339-1
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The resolution of asymmetrically substituted dibenzophospholes via chromatographic separation of their cyclopalladium derivatives is described for the first time. The absolute configuration of the phosphorus atom was determined by X-ray crystallographic analysis in one case. A general NMR criterion for the complete determination of the configuration of this group of products is proposed. The enantiomeric excess of the resolved compounds was determined by NMR Eu(III) chemical displacement experiments and by HPLC using a chiral stationary phase. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：1987 / 1997
页数：11
相关论文
共 50 条
  • [1] Synthesis of asymmetric dibenzophosphole 5-oxides:: The first dibenzophosphole-based family of compounds with liquid crystalline behaviour
    Durán, E
    Velasco, D
    López-Calahorra, F
    HETEROCYCLES, 2002, 57 (05) : 825 - 855
  • [2] DETERMINATION OF OPTICAL PURITY AND ABSOLUTE CONFIGURATION OF ENANTIOMERIC ARALKYLAMINES
    HOYER, GA
    SEEGER, A
    RUFER, C
    ROSENBER.D
    TETRAHEDRON LETTERS, 1972, (11) : 985 - &
  • [3] NEW CHIRAL REAGENT FOR DETERMINATION OF ENANTIOMERIC PURITY AND ABSOLUTE CONFIGURATION
    POHL, LR
    TRAGER, WF
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1971, (NSEP): : 60 - &
  • [4] A convenient application of the NMR and CD methodologies for the determination of enantiomeric ratio and absolute configuration of chiral atropoisomeric phosphine oxides
    Demchuk, Oleg M.
    Swierczynska, Wioleta
    Pietrusiewicz, K. Michal
    Woznica, Magdalena
    Wojcik, Dominik
    Frelek, Jadwiga
    TETRAHEDRON-ASYMMETRY, 2008, 19 (20) : 2339 - 2345
  • [5] Synthesis of alkyldibenzophosphole 5-oxides
    Durán, E
    Velasco, D
    López-Calahorra, F
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (04): : 591 - 594
  • [6] The determination of enantiomeric purity and absolute configuration by vibrational circular dichroism spectroscopy
    Nafie, LA
    Long, FJ
    Freedman, TB
    Buijs, H
    Rilling, A
    Roy, JR
    Dukor, RK
    FOURIER TRANSFORM SPECTROSCOPY, 1998, (430): : 432 - 434
  • [7] DETERMINATION OF THE ABSOLUTE-CONFIGURATION AND ENANTIOMERIC PURITY OF ALLYLIC AND ACETYLENIC ALCOHOLS
    YASUHARA, F
    YAMAGUCHI, S
    TAKEDA, M
    ABE, T
    MIYANO, S
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1991, 64 (11) : 3390 - 3394
  • [8] Preparation of (+)-chlorofluoroiodomethane, determination of its enantiomeric excess and of its absolute configuration
    Crassous, J
    Jiang, ZJ
    Schurig, V
    Polavarapu, PL
    TETRAHEDRON-ASYMMETRY, 2004, 15 (13) : 1995 - 2001
  • [9] Absolute Configuration Determination Using Enantiomeric Pairs of Molecularly Imprinted Polymers
    Meador, Danielle S.
    Spivak, David A.
    ORGANIC LETTERS, 2014, 16 (05) : 1402 - 1405
  • [10] DETERMINATION OF 5-OXIDES OF PHARMACEUTICALLY IMPORTANT PHENOTHIAZINES BY MEANS OF DIFFERENTIAL PULSE POLAROGRAPHY
    UNDERBERG, WJM
    EBSKAMP, AJF
    PILLEN, JMH
    FRESENIUS ZEITSCHRIFT FUR ANALYTISCHE CHEMIE, 1977, 287 (4-5): : 296 - 297
12345