Full Paper

Preparation of planar-chiral multidonor phosphanylferrocene carboxamides and their application as ligands for palladium-catalysed asymmetric allylic alkylation

  1. Martin Lamač1,
  2. Jiří Tauchman1,
  3. Sascha Dietrich2,
  4. Ivana Císařová1,
  5. Heinrich Lang2,
  6. Petr Štěpnička1,*

Article first published online: 22 JAN 2010

DOI: 10.1002/aoc.1616

Issue

Applied Organometallic Chemistry

Applied Organometallic Chemistry

Volume 24, Issue 4, pages 326–331, April 2010

Additional Information

How to Cite

Lamač, M., Tauchman, J., Dietrich, S., Císařová, I., Lang, H. and Štěpnička, P. (2010), Preparation of planar-chiral multidonor phosphanylferrocene carboxamides and their application as ligands for palladium-catalysed asymmetric allylic alkylation. Applied Organometallic Chemistry, 24: 326–331. doi: 10.1002/aoc.1616

Author Information

  1. 1

    Charles University in Prague, Faculty of Science, Department of Inorganic Chemistry, Hlavova 2030, 128 40 Prague, Czech Republic

  2. 2

    Chemnitz University of Technology, Faculty of Natural Sciences, Institute of Chemistry, Department of Inorganic Chemistry, Straße der Nationen 62, 09111 Chemnitz, Germany

*Department of Inorganic Chemistry, Faculty of Science, Charles University, Hlavova 2030, 12840 Prague, Czech Republic.

Publication History

  1. Issue published online: 15 MAR 2010
  2. Article first published online: 22 JAN 2010
  3. Manuscript Accepted: 7 DEC 2009
  4. Manuscript Revised: 28 OCT 2009
  5. Manuscript Received: 9 OCT 2009

Funded by

  • Czech Science Foundation. Grant Number: 104/09/0561
  • Ministry of Education of the Czech Republic. Grant Numbers: LC06070, MSM0021620857

SEARCH

SEARCH BY CITATION

ARTICLE TOOLS

View Full Article (HTML) Get PDF (236K)

Keywords:

  • ferrocene;
  • phosphanes;
  • carboxamides;
  • PAMAM;
  • palladium;
  • asymmetric allylic alkylation

Graphical Abstract

Thumbnail image of graphical abstract

Enantioselectivities up to 93% ee have been obtained in palladium-catalysed asymmetric allylic alkylation of 1,3-diphenylallyl acetate with amido-phosphanes possessing one to three planar-chiral (Sp)-2-(diphenylphosphanyl)ferrocen-1-yl pendant groups as the ligands.

Abstract

Amide coupling of (Sp)-2-(diphenylphosphanyl)ferrocene-1-carboxylic acid with appropriate terminal amines mediated by 1-hydroxybenzotriazole and a carbodiimide affords multi-donor amides terminally functionalized with planar-chiral (Sp)-2-(diphenylphosphanyl)ferrocen-1-yl moieties in good to excellent yields. Palladium catalysts based on these ligands efficiently promote asymmetric allylic alkylation of 1,3-diphenylallyl acetate with in situ generated dimethyl malonate anion to give the C-alkylated product with ees up to 93% at room temperature. Copyright © 2010 John Wiley & Sons, Ltd.

View Full Article (HTML) Get PDF (236K)