DIOXOLANNES CHIRAUX DERIVES DE L'ACIDE (-)SHIKIMIQUE. DETERMINATION PAR RMN 1H 2D ET 13C DE LA CONFIGURATION DU CENTRE ASYMETRIQUE CREE

Article abstract of DOI:10.1016/S0040-4039(00)80545-6

Chiral dioxolans have been synthesized from (-)methyl shikimate and β-ketoesters in order to mimic the enolization process postulated in the enzyme dehydroquinate hydrolyase mechanism.We expect the (R) isomers to be better recognized by the enzyme.The configuration of the newly created asymmetric center in the dioxolan has been determined by 2D ¹H and ¹³C NMR