Development of cascade type reactions based on Brook rearrangement

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The target of this study is to develop new methodologies for the molecular transformation based on the intramolecular silyl group rearrangement reaction, so-called Brook rearrangement.In searching for various conditions, the reaction of silylated conjugated olefins with phosphine nucleophiles which afforded phosphonium ylides through 1,4-Brook rearrangement was found. A Wittig reaction of the resulting phosphonium ylides and aldehydes proceeded successively and afforded silyl dienol ethers in high efficiency.Furthermore, this sequential reaction methodology could be applied to the reaction of an acyl silane.