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790 SPECIAL TOPIC Indium(I)-Mediated, Tandem Carbonyl Addition-Oxy-Cope Rearrangement of g-Pentadienyl Anions to Cyclohexenones and Conjugated Aromatic Ketones

By Oxy-cope Rearrangement, P. Villalva-servín, A. Melekov and Alex G. Fallis


Abstract: Treatment of 5-bromopenta-1,3-diene with indium metal in the presence of a,b-unsaturated ketones results in initial g-pentadienylation to generate the hydroxy-1,4-diene. In the case of aromatic conjugated ketones or cyclohexenones the indium alkoxide undergoes spontaneous oxy-Cope rearrangement to afford the 1,4addition product. The second double bond is required for this [3,3] sigmatropic rearrangement as allyl groups fail to under go this in situ rearrangement. This behavior is consistent with an indium(I) pentadiene species and appears to be the first example of an indiummediated oxy-Cope rearrangement. Key words: indium, oxy-Cope, [3,3] sigmatropic rearrangement, g-pentadienyl, conjugate addition Previously we have established that treatment of 5-bromopenta-1,3-diene (1) with indium metal, in DMF, DMSO, or water, in the presence of carbonyl compound

Year: 2003
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