Practical, highly active, and enantioselective ferrocenyl-imidazoline palladacycle catalysts (FIPs) for the aza-claisen rearrangement of N-para-methoxyphenyl trifluoroacetimidates

被引:125
作者
Weiss, Matthias E. [1 ]
Fischer, Daniel F. [1 ]
Xin, Zhuo-Qun [1 ]
Jautze, Sascha [1 ]
Schweizer, W. Bernd [1 ]
Peters, Ren [1 ]
机构
[1] ETH, Organ Chem Lab, CH-8093 Zurich, Switzerland
关键词
aza-Claisen rearrangement; cyclopalladation; ferrocene; imidazoline; Overman rearrangement;
D O I
10.1002/anie.200601731
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Just a pinch of catalyst: Just 0.05 mol % of a novel planar chiral ferrocenyl-imidazoline palladacycle catalyst (FIP) is sufficient to catalyze a highly efficient aza-Claisen rearrangement of N-para-methoxyphenyl trifluoroacetimidates and thereby provide access to chiral protected primary allylic amines with unprecedentedly high enantioselectivities (see scheme). (Chemical Equation Presented). © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:5694 / 5698
页数:5
相关论文
共 18 条
  • [1] Catalytic asymmetric rearrangement of allylic trichloroacetimidates. A practical method for preparing allylic amines and congeners of high enantiomeric purity
    Anderson, CE
    Overman, LE
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (41) : 12412 - 12413
  • [2] Catalytic asymmetric synthesis of chiral allylic amines. Evaluation of ferrocenyloxazoline palladacycle catalysts and imidate motifs
    Anderson, CE
    Donde, Y
    Douglas, CJ
    Overman, LE
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (02) : 648 - 657
  • [3] [Anonymous], FERROCENES
  • [4] The syntheses and catalytic applications of unsymmetrical ferrocene ligands
    Atkinson, RCJ
    Gibson, VC
    Long, NJ
    [J]. CHEMICAL SOCIETY REVIEWS, 2004, 33 (05) : 313 - 328
  • [5] Svnthesis of a new chiral N,N,N-tridentate pyridinebisimidazoline ligand library and its application in Ru-catalyzed asymmetric epoxidation
    Bhor, S
    Anilkumar, G
    Tse, MK
    Klawonn, M
    Dobler, C
    Bitterlich, B
    Grotevendt, A
    Beller, M
    [J]. ORGANIC LETTERS, 2005, 7 (16) : 3393 - 3396
  • [6] Probing electronic effects in the asymmetric Heck reaction with the BIPI ligands
    Busacca, CA
    Grossbach, D
    So, RC
    O'Brien, EM
    Spinelli, EM
    [J]. ORGANIC LETTERS, 2003, 5 (04) : 595 - 598
  • [7] Asymmetric [3.3]-sigmatropic rearrangements in organic synthesis
    Enders, D
    Knopp, M
    Schiffers, R
    [J]. TETRAHEDRON-ASYMMETRY, 1996, 7 (07) : 1847 - 1882
  • [8] CIS- EFFECT OF LIGANDS AND TRANS-EFFECTS OF LIGANDS
    HARTLEY, FR
    [J]. CHEMICAL SOCIETY REVIEWS, 1973, 2 (02) : 163 - 179
  • [9] Palladium catalyzed enantioselective rearrangement of allylic imidates to allylic amides
    Hollis, TK
    Overman, LE
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 576 (1-2) : 290 - 299
  • [10] Monomeric cobalt oxazoline palladacycles (COP). Useful catalysts for catalytic asymmetric rearrangement of allylic trichloroacetimidates
    Kirsch, SF
    Overman, LE
    Watson, MP
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (23) : 8101 - 8104