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Selective Indium-Mediated 1,2,4-Pentatrien-3-ylation of Carbonyl Compounds for the Efficient Synthesis of Vinyl Allenols

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journal contribution
posted on 06.11.2008, 00:00 by Jisu Park, Sung Hong Kim, Phil Ho Lee
A highly selective synthetic method of functionalized vinyl allenols was developed from the reactions of various carbonyl compounds with organoindium reagent in situ generated from indium and 1-bromopent-4-en-2-yne derivatives. Treatment of vinyl allenols with gold catalyst, dienophile, or indium trihalide produced the functionalized dihydrofuran, cyclohexene, or 2-halo-1,3-diene derivatives in good to excellent yields.