Development and Mechanistic Studies of Oxidative Prins-Semipinacol Cyclization Reactions

Key Points

• The aim is to investigate the mechanistic pathways of oxidative Prins-semipinacol reactions and their efficiency in constructing spirocyclic ethers.
• Utilized allylic alcohols and silyl ethers as reactants.
• Conducted a kinetic isotope effect study to analyze rate-determining steps.
• Examined stereoselective construction pathways.
• Demonstrated carbon-carbon and carbon-oxygen bond formation through the reactions.
• Identified hydride abstraction as the rate-determining step.
• Showed that distal nucleophilic groups lower the transition state free energy.

Abstract