Novel ferrocenyl ligands with planar and central chirality in Pd-catalyzed allylic substitutions

被引:58
|
作者
Enders, D [1 ]
Peters, R [1 ]
Runsink, J [1 ]
Bats, JW [1 ]
机构
[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
关键词
D O I
10.1021/ol991139l
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] The use of planar chiral ferrocenyl ligands bearing a stereogenic center in beta-position of the side chain was investigated in Pd-catalyzed enantioselective allylic substitutions. By employing 2.2 mol % of a P,S-ligand and 1.0 mol % of [Pd(eta(3)-C3H5)Cl](2), the alkylation of the standard test system (+/-) (E)-diphenyl-2-propenyl acetate using dimethylmalonate/BSA as nucleophile proceeded in quantitative yield with an ee of 97%, which is the best value reported so far in this reaction using a P,S-ligand.
引用
收藏
页码:1863 / 1866
页数:4
相关论文
共 50 条
  • [11] Immobilization of chiral ferrocenyl ligands on silica gel and their testing in Pd-catalyzed allylic substitution and Rh-catalyzed hydrogenation
    Cvengros, J
    Toma, S
    Zembéryová, M
    Macquarrie, DJ
    MOLECULES, 2005, 10 (06): : 679 - 692
  • [12] Chiral pyridinyloxazolidine ligands for the Pd-catalyzed asymmetric allylic alkylation
    Yoon, JK
    Lee, SJ
    Kim, YM
    Jin, MJ
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2003, 24 (09) : 1239 - 1240
  • [13] Novel pyridine-phosphite ligands for Pd-catalyzed asymmetric allylic substitution reaction
    Meng, Xiangyan
    Gao, Yongguang
    Li, Xinsheng
    Xu, Dongcheng
    CATALYSIS COMMUNICATIONS, 2009, 10 (06) : 950 - 954
  • [14] Amino-P Ligands from Iminosugars: New Readily Available and Modular Ligands for Enantioselective Pd-Catalyzed Allylic Substitutions
    Borras, Carlota
    Elias-Rodriguez, Pilar
    Carmona, Ana T.
    Robina, Inmaculada
    Pamies, Oscar
    Dieguez, Montserrat
    ORGANOMETALLICS, 2018, 37 (11) : 1682 - 1694
  • [15] Origin of Stereoselectivity in Pd-Catalyzed Asymmetric Allylic Substitutions with Trost-Type Mixed Bidentate Phosphorus Ligands
    Seo, Sanghyup
    Shin, Taeil
    Choi, Inkyu
    Kim, Hyunwoo
    ACS CATALYSIS, 2024, 14 (14): : 11113 - 11120
  • [16] Synthesis of novel carbohydrate-based iminophosphinite ligands in Pd-catalyzed asymmetric allylic alkylations
    Shen, Chao
    Xia, Haijun
    Zheng, Hui
    Zhang, Pengfei
    Chen, Xinzhi
    TETRAHEDRON-ASYMMETRY, 2010, 21 (15) : 1936 - 1941
  • [17] Novel planar chiral phosphite: Preparation and use in the synthesis of Pd(II) complexes and in Pd-catalyzed allylic alkylation
    Tsarev, V. N.
    Konkin, S. I.
    Loim, N. M.
    Kelbysheva, E. S.
    Popova, L. N.
    Petrovskii, P. V.
    Davankov, V. A.
    Gavrilov, K. N.
    RUSSIAN JOURNAL OF COORDINATION CHEMISTRY, 2007, 33 (09) : 656 - 660
  • [18] Synthesis of novel ferrocenylphosphine-amidine ligands and their application in Pd-catalyzed asymmetric allylic alkylation
    Hu, XP
    Chen, HL
    Hu, XQ
    Dai, HC
    Bai, CM
    Wang, JW
    Zheng, Z
    TETRAHEDRON LETTERS, 2002, 43 (50) : 9179 - 9182
  • [19] Novel planar chiral phosphite: Preparation and use in the synthesis of Pd(II) complexes and in Pd-catalyzed allylic alkylation
    V. N. Tsarev
    S. I. Konkin
    N. M. Loim
    E. S. Kelbysheva
    L. N. Popova
    P. V. Petrovskii
    V. A. Davankov
    K. N. Gavrilov
    Russian Journal of Coordination Chemistry, 2007, 33 : 656 - 660
  • [20] CHIRAL PHOSPHINOARYLDIHYDROOXAZOLES AS LIGANDS IN ASYMMETRIC CATALYSIS - PD-CATALYZED ALLYLIC SUBSTITUTION
    VONMATT, P
    PFALTZ, A
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1993, 32 (04): : 566 - 568