title: Synthesis of 2-cyclopentenones by gold(I)-catalyzed Rautenstrauch rearrangement.
abstract: The rearrangement of 1-ethynyl-2-propenyl pivaloates to cyclopentenones catalyzed by cationic triphenylphosphinegold(I) complexes is described. The reaction tolerates both alkyl and aryl substitution at the acetylenic and olefinic positions. Importantly, the gold(I)-catalyzed rearrangement of enantioenriched propargyl pivaloates proceeds with excellent chirality transfer, thus providing a practical method for the enantioselective synthesis of cyclopentenones.
authors.affiliation: Center for New Directions in Organic Synthesis, Department of Chemistry, University of California, Berkeley, California 94720, USA.
authors.forename: Xiaodong
authors.initials: X
authors.lastname: Shi
authors.forename: David J
authors.initials: DJ
authors.lastname: Gorin
authors.forename: F Dean
authors.initials: FD
authors.lastname: Toste