Work

Development and Mechanistic Studies of Oxidative Prins-Semipinacol Cyclization Reactions

Year: 2026

Type: article

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.

Source: Organic Letters

DOI: 10.1021/acs.orglett.6c00814

Authors: Max O. Kogut, Karen R. Garn, Michael J. Kerner, Paul E. Floreancig

Institution: University of Pittsburgh

Language: English

Topic: Oxidative Organic Chemistry Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funder: Division of Chemistry