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Communication | Special issue | Vol 90, No. 1, 2015, pp.163-171
Published online, 8th August, 2014
DOI: 10.3987/COM-14-S(K)60
Synthesis of α-Halobutenolides Using the Nucleophilicity of Magnesium Alkylidene Carbenoids

Tsutomu Kimura,* Kazuki Fukuda, Gaku Kashiwamura, and Tsuyoshi Satoh*

*Tokyo University of Science, Kagurazaka 1-3, Shinjuku-ku, Tokyo 165-0035, Japan


α-Halobutenolides were synthesized from halomethyl p-tolyl sulfoxides, α-bromoketones, and phenyl chloroformate in three steps using the nucleophilicity of magnesium alkylidene carbenoids. The reaction of α-bromoketones with [halo(p-tolylsulfinyl)methyl]lithiums and the subsequent basification of the reaction mixture using an aqueous NaOH solution afforded 1-chloro-3-hydroxyprop-1-enyl p-tolyl sulfoxides in 83–99% yield. A phenoxycarbonyl group was then introduced to the hydroxyl group of the sulfoxides by reacting with phenyl chloroformate in the presence of pyridine. The sulfoxide/magnesium exchange reaction of the cyclization precursors with i-PrMgCl•LiCl led to the formation of α-halobutenolides in moderate to good yields.