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One-Pot Synthesis of γ,δ-Unsaturated Carbonyl Compounds from Allyl Alcohols and Vinyl or Isopropenyl Acetates Catalyzed by [IrCl(cod)]2

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journal contribution
posted on 04.08.2006, 00:00 authored by Masao Morita, Satoshi Sakaguchi, Yasutaka Ishii
One-pot synthesis of γ,δ-unsaturated carbonyl compounds from allyl alcohols and vinyl or isopropenyl acetates was achieved through in situ generation of allyl vinyl ethers by the action of the [IrCl(cod)]2 complex followed by Claisen rearrangement of the resulting ethers. For instance, the reaction of trans-2-methyl-3-phenyl-2-propen-1-ol with isopropenyl acetate in the presence of [IrCl(cod)]2 (1 mol %) and Cs2CO3 (5 mol %) at 100 °C for 3 h followed by 140 °C for 15 h afforded 5-methyl-4-phenyl-5-hexen-2-one in 72% yield. When vinyl acetate was employed in place of isopropenyl acetate, 4-methyl-3-phenyl-4-pentenal was obtained in 83% yield.

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