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Paper | Special issue | Vol 61, No. 1, 2003, pp.365-376
Published online, 2nd October, 2003
DOI: 10.3987/COM-03-S52
Synthesis and Reaction of Bromoallylsilane: A Short Access to β,γ-Disubstituted α-Methylene-γ-butyrolactone

Jun’ichi Uenishi* and Masashi Ohmi

*Kyoto Pharmaceutical University, Misasagi, Yamashina, Kyoto 607-8414, Japan

Abstract

(Z)-β-Bromoallylsilanes (1a-c) were prepared by a stereoselective Ni-catalyzed cross-coupling reaction of 1,1-dibromo-4-phenylbutene (4) with silylmethylmagnesium halide. Sakurai-Hosomi reaction of 1a with aldehyde gave syn-3-alkyl-2-bromo-4-hydroxyalkene (2a, 2c, and 2e) and that with acetal gave syn-4-alkoxy-3-alkyl-2-bromoalkene (2b and 2d) stereoselectively. The products with formyl function reacted with a Ni-carbonyl complex to give β,γ-disubstituted α-methylene-γ-butyrolactones (3) in good yields. Pd-catalyzed cross-coupling reaction of 1a-c or 4 with silylmethylmagnesium halide gave 1,1-bis(silylmethyl)-1-alkenes (1d-i), which reacted with dimethyl acetal to generate more functionalized allylsilane (6).