REGIOCHEMICAL CONTROL OF THE RING-OPENING OF 1,2-EPOXIDES BY MEANS OF CHELATING PROCESSES .10. SYNTHESIS AND RING-OPENING REACTIONS OF MONOFUNCTIONALIZED AND DIFUNCTIONALIZED CIS AND TRANS ALIPHATIC OXIRANE SYSTEMS

The regiochemical outcome of the ring opening of 1,2-epoxides through chelation processes assisted by metal ions, was verified in mono- and difunctionalized aliphatic oxirane systems bearing the heterofunctionality (OR) in an homoallylic and/or allylic relationship to the oxirane ring. The effect of the distance of the OR functionality from the oxirane ring and of the type of protective group on the regiochemical outcome of these systems is examined. In some cases, the use of LiClO4 or Mg(ClO4)(2) as the promoting metal salt makes it possible the obtainment of a nice regioalternating process.