Synthesis and resolution of benzylisopropylphenylphosphine a monodentate P-chiral ligand

被引:35
|
作者
Albert, J [1 ]
Bosque, R [1 ]
Cadena, JM [1 ]
Granell, JR [1 ]
Muller, G [1 ]
Ordinas, JI [1 ]
机构
[1] Univ Barcelona, Dept Quim Inorgan, E-08028 Barcelona, Spain
关键词
D O I
10.1016/S0957-4166(00)00300-1
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The synthesis of benzylisopropylphenylphosphine by reaction between the benzylphenylphosphide anion and isopropyl chloride and its subsequent resolution by means of an optically active palladium metallacycle is reported. The synthesis of the organometallic complex [Pd(eta(3)-2-MeC3H4)Cl((PBnPrPh)-Pr-i)] is also described, as well as the assignment of the absolute configuration of the coordinated phosphine by mono- and bidimensional proton NMR spectra, using the homochiral palladacycle as a reference point. In order to estimate the height of the energy barrier corresponding to the rotation of the phosphine ligand around the Pd-P bond, several calculations were performed at the semiempirical PM3(tm) level. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3335 / 3343
页数:9
相关论文
共 50 条
  • [1] Synthesis, resolution, and reactivity of benzylmesitylphenylphosphine: A new P-chiral bulky ligand
    Albert, J
    Bosque, R
    Cadena, JM
    Delgado, S
    Granell, J
    Muller, G
    Ordinas, JI
    Bardia, MF
    Solans, X
    CHEMISTRY-A EUROPEAN JOURNAL, 2002, 8 (10) : 2279 - 2287
  • [2] Synthesis and resolution of a new P-chiral hydroxy phosphine
    Albert, J
    Cadena, JM
    Delgado, S
    Granell, J
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2000, 603 (02) : 235 - 239
  • [3] Stereoselective synthesis and resolution of P-chiral phosphine chalcogenides.
    Pietrusiewicz, KM
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1996, 109 (1-4) : 573 - 576
  • [4] P-chiral, monodentate ferrocenyl phosphines, novel ligands for asymmetric catalysis
    Colby, EA
    Jamison, TF
    JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (01): : 156 - 166
  • [5] P-Chiral monodentate diamidophosphites as ligands for Rh-catalyzed asymmetric reactions
    S. E. Lyubimov
    V. A. Davankov
    P. V. Petrovskii
    N. M. Loim
    Russian Chemical Bulletin, 2007, 56 : 2094 - 2096
  • [6] P-Chiral monodentate diamidophosphites as ligands for Rh-catalyzed asymmetric reactions
    Lyubimov, S. E.
    Davankov, V. A.
    Petrovskii, P. V.
    Loim, N. M.
    RUSSIAN CHEMICAL BULLETIN, 2007, 56 (10) : 2094 - 2096
  • [7] OxaPhos: A new class of tunable, P-chiral, monodentate ligands for enantioselective catalysis
    Schuster, Christopher H.
    Morken, James P.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
  • [8] A versatile and efficient approach to enantiomerically pure monodentate and bidentate P-chiral phosphines
    Leung, PH
    Liu, AM
    Mok, KF
    TETRAHEDRON-ASYMMETRY, 1999, 10 (07) : 1309 - 1314
  • [9] Synthesis of P-chiral enephosphonic acid derivatives
    Grison, C
    Comoy, C
    Chatenet, D
    Coutrot, P
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 662 (1-2) : 83 - 97
  • [10] A RESOLUTION OF MONODENTATE P-ASTERISK CHIRAL PHOSPHINE
    DUNINA, VV
    GOLOVAN, EB
    TETRAHEDRON-ASYMMETRY, 1995, 6 (11) : 2747 - 2754