A SIMPLE ROUTE TO AN ENANTIOMERICALLY PURE DIPHOSPHINE LIGAND CONTAINING A PHOSPHORUS STEREOGENIC CENTER

被引:35
作者
AW, BH [1 ]
LEUNG, PH [1 ]
机构
[1] NATL UNIV SINGAPORE,DEPT CHEM,SINGAPORE 0511,SINGAPORE
关键词
D O I
10.1016/0957-4166(94)80148-7
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The (+)- and (-)- forms of 5-(diphenylphosphino)-2,3-dimethyl-7-phenyl-7-phosphabicyclo[2.2.1]hept-2-ene have been prepared enantioselectively via an asymmetric Diels-Alder reaction between diphenylvinylphosphine and 1-phenyl-3,4-dimethylphosphole (DMPP) using 0.5 equiv of (R)-(-)- and (S)-(+)-bis(mu-chloro)bis[1-[1-(dimethylamino)ethyl]-2-naphthalenyl-C,N]dipalladium(II), respectively, as the chiral catalyst. The enantiomeric purity of the diphosphine ligand has been confirmed by H-1 and P-31 NMR studies.
引用
收藏
页码:1167 / 1170
页数:4
相关论文
共 10 条
  • [1] RESOLUTIONS INVOLVING METAL COMPLEXATION - PREPARATION AND RESOLUTION OF (R,S)-METHYLPHENYL(8-QUINOLYL)PHOSPHINE AND ITS ARSENIC ANALOG - CRYSTAL AND MOLECULAR-STRUCTURE OF (+)589-[(R)-DIMETHYL(1-ETHYL-ALPHA-NAPHTHYL)AMINATO-C-2, N][(S)-METHYLPHENYL(8-QUINOLYL)PHOSPHINE]PALLADIUM(II) HEXAFLUOROPHOSPHATEOG
    ALLEN, DG
    MCLAUGHLIN, GM
    ROBERTSON, GB
    STEFFEN, WL
    SALEM, G
    WILD, SB
    [J]. INORGANIC CHEMISTRY, 1982, 21 (03) : 1007 - 1014
  • [2] BOSNICH B, 1986, ASMMETRIC CATALYSIS, pCH1
  • [3] VERSATILE CHIRAL PALLADIUM(II) COMPLEXES FOR ENANTIOMERIC PURITIES OF 1,2-DIAMINES
    CHOOI, SYM
    LEUNG, PH
    LIM, CC
    MOK, KF
    QUEK, GH
    SIM, KY
    TAN, MK
    [J]. TETRAHEDRON-ASYMMETRY, 1992, 3 (04) : 529 - 532
  • [4] HOMER L, 1966, TETRAHEDRON LETT, P5783
  • [5] EFFICIENT ASYMMETRIC-SYNTHESIS OF OPTICALLY PURE TERTIARY MONO AND DIPHOSPHINE LIGANDS
    JUGE, S
    STEPHAN, M
    LAFFITTE, JA
    GENET, JP
    [J]. TETRAHEDRON LETTERS, 1990, 31 (44) : 6357 - 6360
  • [6] KAGAN HB, 1990, CHEM ORGANOPHOSPHORU, pCH3
  • [7] RESOLUTIONS INVOLVING METAL COMPLEXATION - OPTICAL RESOLUTION AND PHOTOCHEMICAL-REARRANGEMENT OF (+/-)-(2-MERCAPTOETHYL)METHYLPHENYLPHOSPHINE
    LEUNG, PH
    WILLIS, AC
    WILD, SB
    [J]. INORGANIC CHEMISTRY, 1992, 31 (08) : 1406 - 1410
  • [8] INTRAMOLECULAR [4 + 2] DIELS-ALDER CYCLO-ADDITION REACTIONS OF PHOSPHOLES WITH VINYLPHOSPHINES PROMOTED BY PALLADIUM AND PLATINUM
    RAHN, JA
    HOLT, MS
    GRAY, GA
    ALCOCK, NW
    NELSON, JH
    [J]. INORGANIC CHEMISTRY, 1989, 28 (02) : 217 - 226
  • [9] RESOLUTIONS USING METAL-COMPLEXES - SYNTHESIS, SEPARATION INTO DIASTEREOISOMERS, AND RESOLUTION OF ORTHO-PHENYLENEBIS(METHYLPHENYLPHOSPHINE) USING PALLADIUM COMPLEXES CONTAINING OPTICALLY-ACTIVE ORTHO-METALLATED DIMETHYL(ALPHA-METHYLBENZYL)AMINES
    ROBERTS, NK
    WILD, SB
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (21) : 6254 - 6260
  • [10] RUTHENIUM(II)-PROMOTED SITE-SELECTIVE INTRAMOLECULAR DIELS-ALDER REACTIONS
    VAC, R
    NELSON, JH
    MILOSAVLJEVIC, EB
    SOLUJIC, L
    FISCHER, J
    [J]. INORGANIC CHEMISTRY, 1989, 28 (22) : 4132 - 4139