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

Jisu Park, Sung Hong Kim and Phil Ho Lee*

*National Research Laboratory for Catalytic Organic Reaction, Department of Chemistry, and Institute for Molecular Science and Fusion Technology, Kangwon National University, Chuncheon 200-701, Republic of Korea, Email: phleekangwon.ac.kr

J. Park, S. Hong, P. H. Lee, Org. Lett., 2008, 10, 5067-5070.

DOI: 10.1021/ol802073q

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Abstract

Reactions of various carbonyl compounds with organoindium reagent in situ generated from indium and 1-bromopent-4-en-2-yne derivatives gives functionalized vinyl allenols in good yields. Treatment of vinyl allenols with gold catalyst, dienophile, or indium trihalide produced functionalized dihydrofuran, cyclohexene, or 2-halo-1,3-diene derivatives in very good yields.

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Efficient Synthetic Method of Multisubstituted Allenes from the Reactions of Allylindium Reagents with 3°-Propargyl Alcohols

K. Lee, P. H. Lee, Org. Lett., 2008, 10, 2441-2444.

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Key Words

allenes, allylic alcohols, indium

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ID: J54-Y2008-3400