Heterocyclic Communications p. 249 - 252 (2001)
Update date:2022-08-17
Topics:
De Mattos, Marcio C.S.
De Souza, Soraia P.L.
Elias, Simone M.
Transition metal salts mediated oxidative radical addition of ethyl acetoacetate to limonene produced chemo-and regiospecificaly (1'R,5RS)-3-carboethoxy-2,5-dimethyl-5-(4'-methylcyclohexen-3'-enyl)-4,5- dihydrofuran as a 1:1 mixture of diastereoisomers. The best yield (72 % isolated) was obtained using limonene (1 mol equiv.), ethyl acetoacetate (1 mol equiv.) and Mn(OAc)3?2H2O (2 mol equiv.) in acetic acid at 70°C. The utilisation of cerium(IV) ammonium nitrate (CAN) or Co(OAc)2 instead of Mn(III) led to lower yields of the dihydrofurans along with diethyl 2,3-diacetylsuccinate. Fe(III) salts gave a complex mixture of products and using CuCl2 there was no reaction.
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