What question did this study set out to answer?

The aim is to investigate the mechanistic pathways of oxidative Prins-semipinacol reactions and their efficiency in constructing spirocyclic ethers.

April 15, 2026Open Access

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

This work shows that allylic alcohols or silyl ethers promote hydride abstraction leading to direct carbon-carbon bond formation or carbon-oxygen bond formation followed by rearrangement, providing the stereoselective construction of spirocyclic ethers through a Prins-semipinacol pathway. A kinetic isotope effect study showed that hydride abstraction is the rate-determining step, consistent with the presence of a distal nucleophilic group lowering the transition state free energy of the oxidation step.

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Cite This Study

Kogut et al. (Sun,) studied this question.

synapsesocial.com/papers/69df2c62e4eeef8a2a6b1682 https://doi.org/https://doi.org/10.1021/acs.orglett.6c00814

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