Download PDF
Synfacts 2007(9): 0970-0970  
DOI: 10.1055/s-2007-968818
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Au(I)-Catalyzed Rearrangement of Allylic Acetates

Contributor(s): Paul Knochel, Tobias Thaler
N. Marion, R. Gealageas, S. P. Nolan*
Institute of Chemical Research of Catalonia, Tarragona, Spain
Further Information

Publication History

Publication Date:
23 August 2007 (online)

    Permissions and Reprints

Significance

An efficient [(NHC)AuCl]-catalyzed (NHC: N-heterocyclic carbene) rearrangement of allylic acetates is presented. The reaction disposes of a broad substrate scope and the respective products are received with good diastereomeric ratios. It is noteworthy that sterically demanding moieties on the N-heterocyclic carbene ligand are necessary for the reaction to proceed. It is assumed that Au(I) is thus protected from forming unreactive Au(0) clusters.