Synlett

Synthesis of (2-Arylethylidene) cyclobutanes by Palladium-Catalyzed Reactions of Aryl Halides with Homoallyl Alcohols Bearing a Trimethylene Group at the Allylic …

M Iwasaki, H Yorimitsu, K Oshima

Index: Iwasaki, Masayuki; Yorimitsu, Hideki; Oshima, Koichiro Synlett, 2009 , # 13 p. 2177 - 2179

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Citation Number: 4

Abstract

Abstract Treatment of aryl bromides with homoallyl alcohols bearing a trimethylene group at the allylic position in the presence of cesium carbonate under palladium catalysis affords (2- arylethylidene) cyclobutanes selectively. The selective formation of the alkylidenecyclobutane skeleton results from regiospecific retro-allylation of the homoallyl alcohols, which accompanies the transposition of the double bonds.