Tetrahedron Letters p. 3127 - 3130 (1991)
Update date:2022-08-04
Topics:
Lange, J. H. M.
Sommerdijk, N. A. J. M.
Dols, P. P. M. A.
Arnouts, E. G.
Klunder, A. J. H.
Zwanenburg, B.
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.
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