Organic letters

Selective indium-mediated 1, 2, 4-pentatrien-3-ylation of carbonyl compounds for the efficient synthesis of vinyl allenols

J Park, SH Kim, PH Lee

Index: Park, Jisu; Kim, Sung Hong; Lee, Phil Ho Organic Letters, 2008 , vol. 10, # 21 p. 5067 - 5070

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Citation Number: 23

Abstract

ABSTRACT 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.