4.5 Article

Imidate-Phosphanes as Highly Versatile N,P Ligands and Their Application in Palladium-Catalyzed Asymmetric Allylic Alkylation Reactions

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2010, Issue 21, Pages 4056-4061

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201000238

Keywords

Asymmetric catalysis; N,P ligands; Palladium; Allylic alkylation; Imidate ligands

Funding

  1. Ghent University
  2. European Cooperation in Science and Technology (COST)

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Chiral imidate-phosphanes were developed as a new type of N,P ligands. These ligands are easily accessible through a one-step procedure starting from a commercially available chiral aminophosphane and an imidate precursor. Excellent performance of the catalyst system was observed with various carbon nucleophiles in the Pd-0-catalyzed asymmetric allylic alkylation (up to 99% yield and >99 % ee). Moreover, good to excellent enantioselectivities could also be obtained in the allylic alkylation of more difficult linear unhindered substrates and cyclic substrates, demonstrating that this new catalyst system has a broad substrate scope.

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