Journal of Organic Chemistry p. 4444 - 4448 (1980)
Update date:2022-08-30
Topics:
Hudrlik, Paul F.
Hudrlik Anne M.
Misra, Raj N.
Peterson, David
Withers, Gregory P.
Kulkarni, Ashok K.
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.
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