Gold(I)/(III)-catalyzed rearrangement of divinyl ketones and acyloxyalkynyloxiranes into cyclopentenones.
Multifaceted gold(I/III) catalysts with their carbophilic and oxophilic characters catalyzed very efficiently the formation of hydroxylated cyclopentenones from simple divinyl ketones or acyloxyalkynyloxiranes. The Nazarov reaction is rapidly performed in dichloroethane with 5 mol % of the simple gold(III) trichloride salt at 70 °C, while the rearrangement of alkynyloxiranes requires 5 mol % of a more stable NHC gold(III) triflimidate complex.
Laboratoire de Synthèse, Réactivité Organiques et Catalyse and ‡Laboratoire de Chimie de Coordination, Institut de Chimie, UMR 7177-CNRS, Université de Strasbourg , 4 rue Blaise Pascal, 67070 Strasbourg, France.
Marie
M
Hoffmann
Jean-Marc
JM
Weibel
Pierre
P
de Frémont
Patrick
P
Pale
Aurélien
A
Blanc
D002384:Catalysis; D003500:Cyclization; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry; D004852:Epoxy Compounds / Q000737:chemistry*; D006046:Gold / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry*
D003517:Cyclopentanes; D004852:Epoxy Compounds; D007659:Ketones; D014753:Vinyl Compounds; D006046:Gold; C013905:cyclopentenone