Heterocycles p. 365 - 376 (2003)
Update date:2022-08-03
Topics:
Uenishi, Jun'ichi
Ohmi, Masashi
(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).
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