Journal of Organic Chemistry p. 1026 - 1031 (1985)
Update date:2022-08-05
Topics:
Fristad, William E.
Hershberger, Susan S.
Manganese(III) oxidation of malonic acid in the presence of alkenes results in the formation of spiro-fused lactones, 2,7-dioxaspiro<4.4>nonane-1,6-diones.Terminal alkenes produce a mixture of the three possible diastereomers.The stereochemistry of the diastereomeric spirodilactones was determined by NMR and corroborated by the intensity of the coupled IR carbonyl stretching frequencies. 1,1,6,6-Tetrasubstituted 1,5-hexadienes give in one step tricyclic dilactones.Mechanistic and synthetic aspects of this reaction are discussed.
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