Palladium-catalysed asymmetric allylation and complex formation involving P,N-bidentate diamidophosphites with 1,3,2-diazaphospholidine cycles

被引:2
|
作者
Gavrilov, KN
Tsarev, VN
Zheglov, SV
Lyubimov, SE
Shiryaev, AA
Davankov, VA
机构
[1] Russian Acad Sci, Inst Organoelement Cpds, Moscow 119991, Russia
[2] Ryazan State Pedag Univ, Dept Chem, Ryazan 390000, Russia
基金
俄罗斯基础研究基金会;
关键词
chiral P; N-ligands; diamidophosphites; palladium; rhodium; asymmetric allylation;
D O I
10.1016/j.ica.2004.12.047
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
New chiral P,N-bidentate 1,3,2-diazaphospholidine ligands were obtained by one-step phosphorylation of (2S,3S)-2-(ferroceny-lideneamino)-3-methylpentan-1-ol and (4S,5S)-(-)-2-methyl-4-hydroxymethyl-5-phenyt-2-oxazoline. Complexation of the new ligands with [Rh(CO)(2)Cl](2) and [Pd(allyl)Cl](2) was found to give chelate complexes [Rh(CO)Cl(eta(2)-P,N)] and [Pd(allyl) (eta(2)-P,N)]+BF4-, correspondingly. With the new P,N-ligands, up to 70% ee was achieved in the asymmetric Pd-catalysed sulfonylation of 1,3-diphenyl-2-propenyl acetate with sodium p-toluenesulfinate. In the enantioselective alkylation of 1,3-diphenyl-2-propenyl acetate with dimethyl malonate, up to 91% enantioselectivity was achieved by using [Pd(allyl)(eta(2)-P, N)]+ BF4- complexes as chiral catalysts. (c) 2005 Elsevier B.V. All rights reserved.
引用
收藏
页码:2077 / 2081
页数:5
相关论文
共 11 条
  • [1] Asymmetric Catalytic Reactions Using P*-Mono-, P*,N- and P*,P*-Bidentate Diamidophosphites with BINOL Backbones and 1,3,2-Diazaphospholidine Moieties: Differences in the Enantioselectivity
    Gavrilov, Konstantin N.
    Zheglov, Sergey V.
    Rastorguev, Eugenie A.
    Groshkin, Nikolay N.
    Maksimova, Marina G.
    Benetsky, Eduard B.
    Davankov, Vadim A.
    Reetz, Manfred T.
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (14-15) : 2599 - 2610
  • [2] Palladium-catalyzed asymmetric allylation and complex formation involving P,N-bidentate derivatives of (S)-2-(anilinomethyl)pyrrolidine
    O. G. Bondarev
    K. N. Gavrilov
    V. N. Tsarev
    V. A. Davankov
    R. V. Lebedev
    S. K. Moiseev
    V. N. Kalinin
    [J]. Russian Chemical Bulletin, 2002, 51 : 521 - 525
  • [3] Palladium-catalyzed asymmetric allylation and complex formation involving P,N-bidentate derivatives of (S)-2-(anilinomethyl)pyrrolidine
    Bondarev, OG
    Gavrilov, KN
    Tsarev, VN
    Davankov, VA
    Lebedev, RV
    Moiseev, SK
    Kalinin, VN
    [J]. RUSSIAN CHEMICAL BULLETIN, 2002, 51 (03) : 521 - 525
  • [4] Development of P*-monodentate diamidophosphites with a C1-symmetric 1,2-diamine backbone: the effects of substituents in the 1,3,2-diazaphospholidine cycle on Pd-catalyzed asymmetric allylations
    Gavrilov, Konstantin N.
    Shiryaev, Alexei A.
    Zheglov, Sergey V.
    Potapova, Oksana V.
    Chuchelkin, Ilya V.
    Novikov, Ivan M.
    Rastorguev, Eugenie A.
    Davankov, Vadim A.
    [J]. TETRAHEDRON-ASYMMETRY, 2013, 24 (07) : 409 - 417
  • [5] Palladium-catalyzed allylic substitution assisted by 1,3,2-diazaphospholidine derivatives of (R,R)-N-naphthyltartarimide
    K. N. Gavrilov
    E. A. Rastorguev
    S. V. Zheglov
    N. N. Groshkin
    V. E. Boyko
    A. S. Safronov
    P. V. Petrovskii
    V. A. Davankov
    [J]. Russian Chemical Bulletin, 2010, 59 : 1242 - 1247
  • [6] Palladium-catalyzed allylic substitution assisted by 1,3,2-diazaphospholidine derivatives of (R,R)-N-naphthyltartarimide
    Gavrilov, K. N.
    Rastorguev, E. A.
    Zheglov, S. V.
    Groshkin, N. N.
    Boyko, V. E.
    Safronov, A. S.
    Petrovskii, P. V.
    Davankov, V. A.
    [J]. RUSSIAN CHEMICAL BULLETIN, 2010, 59 (06) : 1242 - 1247
  • [7] Pd-Catalyzed asymmetric transformations involving P☆-mono- and P☆,N-bidentate diamidophosphites derived from (2S,3S)-N2,3-dimethyl-N1-phenylpentane-1,2-diamine
    Gavrilov, K. N.
    Chuchelkin, I. V.
    Zheglov, S. V.
    Shiryaev, A. A.
    Potapova, O. V.
    Novikov, I. M.
    Rastorguev, E. A.
    Petrovskii, P. V.
    Davankov, V. A.
    [J]. RUSSIAN CHEMICAL BULLETIN, 2012, 61 (10) : 1925 - 1932
  • [8] Pd-Catalyzed asymmetric transformations involving P*-mono- and P*,N-bidentate diamidophosphites derived from (2S,3S)-N2,3-dimethyl-N1-phenylpentane-1,2-diamine
    K. N. Gavrilov
    I. V. Chuchelkin
    S. V. Zheglov
    A. A. Shiryaev
    O. V. Potapova
    I. M. Novikov
    E. A. Rastorguev
    P. V. Petrovskii
    V. A. Davankov
    [J]. Russian Chemical Bulletin, 2012, 61 : 1925 - 1932
  • [9] Synthesis and spectral and structural characterization of the palladium(II) complex with a P,N-bidentate ligand based on [(1S)-endo]-(-)-borneol
    Gavrilov, KN
    Mikhel, IS
    Lysenko, KA
    Antipin, MY
    Timofeeva, GI
    Polosukhin, AI
    Korostylev, AV
    [J]. ZHURNAL NEORGANICHESKOI KHIMII, 1997, 42 (04): : 593 - 600
  • [10] STERICALLY PROMOTED N-2 BOUND TETRAZOLATE COMPLEX-FORMATION IN THE 1,3-DIPOLAR CYCLOADDITION OF P-OMEC6H4CN TO THE COORDINATED AZIDE IN THE PALLADIUM COMPLEX [PD(N-N-S)(N3)] - X-RAY CRYSTAL-STRUCTURE OF [PD(N-N-S)(N4C-P-OMEC6H4]
    DAS, R
    PAUL, P
    NAG, K
    [J]. INORGANICA CHIMICA ACTA, 1991, 185 (02) : 221 - 227