Abstract
Abstract The enantioselective synthesis of some β-silyl γ-alkyl γ-butyrolactones has been achieved by an organo-catalyzed Michael addition of enolizable aldehydes onto a silylmethylene malonate followed by a silicon-facilitated Bayer–Villiger oxidation of the β-silyl aldehyde adducts as the key step. γ-Alkyl γ-butenolides were obtained from the β-silyl γ-alkyl γ-butyrolactones by Fleming–Tamao oxidation of the silyl group to a hydroxy group and subsequent elimination. These butenolides are the advanced intermediates of some natural products such as (+)-γ-caprolactone, (+)-methylenolactocine, and (−)-quercus lactone.
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