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
  • [1] Asymmetric synthesis of novel ferrocenyl ligands with planar and central chirality and their application to Pd-catalyzed allylic substitutions
    Enders, D
    Peters, R
    Lochtman, R
    Raabe, G
    Runsink, J
    Bats, JW
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2000, 2000 (20) : 3399 - 3426
  • [2] Synthesis of novel ferrocenylphosphine-amidine ligands with central and planar chirality and their diastereomeric effect in Pd-catalyzed asymmetric allylic alkylation
    Hu, XP
    Chen, HL
    Dai, HC
    Hu, XQ
    Zheng, Z
    TETRAHEDRON-ASYMMETRY, 2003, 14 (14) : 2073 - 2080
  • [3] Synthesis of Novel Ferrocenyl-Based P,S Ligands (ThioClickFerrophos) and Their Use in Pd-Catalyzed Asymmetric Allylic Substitutions
    Kato, Minoru
    Nakamura, Tatsuhito
    Ogata, Kenichi
    Fukuzawa, Shin-ichi
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (30) : 5232 - 5238
  • [4] Novel C2-symmetric planar chiral diphosphine ligands and their application in Pd-catalyzed asymmetric allylic substitutions
    Liu, Delong
    Xie, Fang
    Zhang, Wanbin
    JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (18): : 6992 - 6997
  • [5] Asymmetric synthesis of novel ferrocenyl ligands with planar and central chirality
    Enders, D
    Peters, R
    Lochtman, R
    Raabe, G
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1999, 38 (16) : 2421 - 2423
  • [6] A remarkable anion effect on the enantioselectivity of the Pd-catalyzed allylic amination using ferrocenyl ligands
    Burckhardt, U
    Baumann, M
    Togni, A
    TETRAHEDRON-ASYMMETRY, 1997, 8 (01) : 155 - 159
  • [7] Chiral P,N,N-Ligands for Pd-Catalyzed Asymmetric Allylic Substitutions
    Qin Hao
    Hou Chuanjin
    Liang Dinghua
    He Xinwei
    Li Ling
    Hu Xiangping
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2024, 44 (01) : 282 - 290
  • [8] Asymmetric synthesis of axially chiral anilides by Pd-catalyzed allylic substitutions with P/olefin ligands
    Liu, Yilin
    Feng, Xiangqing
    Du, Haifeng
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (01) : 125 - 132
  • [9] Enantioselective Pd-catalyzed allylic alkylation of Indoles by a new class of chiral ferrocenyl P/S Ligands
    Cheung, Hong Yee
    Yu, Wing-Yiu
    Lam, Fuk Loi
    Au-Yeung, Terry T. -L.
    Zhou, Zhongyuan
    Chan, Tak Hang
    Chan, Albert S. C.
    ORGANIC LETTERS, 2007, 9 (21) : 4295 - 4298
  • [10] Application of SDP Ligands for Pd-catalyzed allylic alkylation
    Xie, JH
    Duan, HF
    Fan, BM
    Cheng, X
    Wang, LX
    Zhou, QL
    ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (06) : 625 - 632