Reactions of α,β-Epoxysilanes with Grignard Reagents. Generation and Trapping of α-Trimethylsilyl Aldehydes and Ketones

Article abstract of DOI:10.1021/jo01310a035

α,β-Epoxysilanes react with Grignard reagents via initial rearrangement to generate α-silyl carbonyl compounds, which are trapped by the Grignard reagent to give β-hydroxysilanes. The reactions of epoxides 8 and 11 take place with very high stereoselectivity to form predominantly erythro β-hydroxysilanes 9 and 12, respectively, which undergo stereospecific β-elimination reactions to give either cis or trans olefins in 96-98percent isomeric purity.