DIASTEREOSELECTIVE SYNTHESIS OF 2,3,4-TRISUBSTITUTED γ-LACTOLS AND γ-LACTONES VIA REGIO- AND STEREOCONTROLLED OPENING OF A 1,2-EPOXY-4-HYDROXYALKYL CARBAMATE WITH HETERO-NUCLEOPHILES

Article abstract of DOI:10.1016/S0040-4039(00)84858-3

The acid-catalyzed ring opening of the title epoxide 1 takes place at the C-1 atom with retention of configuration at C-2 to form 2,3-cis-2-hydroxy-substituted γ-lactol derivatives 3.In basic media, nucleophiles attack the C-2 atom with inversion of confi