REDUCTION DES ANHYDRIDES BICYCLIQUES CONDENSES PAR LE BROMURE DE CYCLOPENTYLMAGNESIUM

Article abstract of DOI:10.1016/S0040-4039(00)94875-5

Greatly different product distributions were observed in the reactions of cyclopentyl- and isopropylmagnesium bromides with cyclohexane-, cyclohex-4-ene- and cyclobutane-1,2 dicarboxylic anhydrides.Cyclopentylmagnesium bromide yielded reduction products with high stereoselectivity whereas the isopropylmagnesium bromide provided the corresponding trans diastereomeric ketoacids via an addition enolization process.