- A new environmentally benign catalytic process for the asymmetric synthesis of lactones: Synthesis of the flavouring δ-decalactone molecule
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The system Sn-Beta/hydrogen peroxide is applied to the Baeyer-Villiger oxidation of delfone to δ-decalactone, which is an industrial fragrance. The reaction is carried out without solvent and with a substrate/catalyst ratio > 200 (wt/wt). Starting with an enantiomerically enriched delfone it is shown that the rearrangement occurs with retention of configuration at the migrating asymmetric carbon atom, and enantiomerically enriched δ-decalactone is obtained as product. This process offers clear advantages over the actual industrial production that uses peracids as oxidants.
- Corma, Avelino,Iborra, Sara,Mifsud, Mari?a,Renz, Michael,Susarte, Manuel
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p. 257 - 262
(2007/10/03)
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- Reactions of Dioxiranes with Selected Oleochemicals
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Reaction of fatty acids with dimethyldioxirane in acetone produces ketoacids in 9-12percent yields in which the ketone carbonyl is distributed along the fatty chain.The n-1 position appears to be preferred.Lactones of hydroxy fatty acids are oxidized by this reagent, but in low yields, to the corresponding ketoacids.Biphasic epoxidations with methylethyldioxirane in 2-butanone were conducted with methyl oleate and methyl ricinoleate to give the corresponding epoxides in high yield, and olive oil and tallow were cleanly epoxidized by this procedure as well.KEY WORDS: Chain functionalization, dioxirane, epoxidation, oleic acid, ricinoleic acid, tallow.
- Sonnet, P. E.,Lankin, M. E.,McNeill, G. P.
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p. 199 - 204
(2007/10/02)
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