Tricyclo[,6]decadienone epoxides: rigid, highly congested α,β-epoxycyclopentanones with distinctive chemical behavior

J.H.M. Lange, N.A.J.M. Sommerdijk, P.P.M.A. Dols, E.G. Arnouts, A.J.H. Klunder, B. Zwanenburg

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Tricyclodecadienone epoxides 5 do not form an enolate on treatment with lithium diisopropyl amide. but instead undergo an unusual stereoselective β-hydride transfer leading to alcohols 6. The same type of epoxy endo-alcohol was obtained from parent epoxy ketone 5 on reaction with metal hydrides and organolithium reagents. These alcohols readily undergo an intramolecular epoxide migration by a Payne-type rearrangement, to give endo-epoxides 9.
Original languageEnglish
Pages (from-to)3127-3130
JournalTetrahedron Letters
Issue number26
Publication statusPublished - 24 Jun 1991
Externally publishedYes

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