Stereoselective synthesis of substituted tetrahydrofurans - Identification and analysis by proton NMR and MNDO, MM2 calculations

Article abstract of DOI:10.1016/S0040-4020(01)80924-8

Methyl acetoacetate and terminal olefins react in the presence of cobalt(II) acetate and oxygen to give 5-alkyl-2-hydroxy-2-methyl-3-methoxycarbonyl tetrahydrofurans in a highly stereoselective manner. Proton NMR, semiempirical MNDO and empirical MM2 methods are used to identify the particular diastereomer and the energetics of the different isomers are discussed.