ArticleJournal of the American Chemical Society2025
Photocatalyzed Epimerization of Quaternary Stereocenters.
Article in Journal of the American Chemical Society, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
What it found
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Who cites it
5 citing papers in PubMed.
- Strategic Applications of Single-Atom Skeletal Editing in Natural Product Synthesis.Journal of the American Chemical Society · 2026Review
- Distance-Dependent, Rate-Accelerating and Diastereoselective Directing Effects in Decatungstate-Mediated Stereoediting Reactions.Journal of the American Chemical Society · 2026Article
- Overriding Stereochemical Outcomes in Cyclase Phase Total Synthesis: Enantioselective Synthesis of Habiterpenol and Dasyscyphin A.Journal of the American Chemical Society · 2026Article
- Recent synthetic methodology advancements towards all-carbon quaternary center formation and applications.Tetrahedron · 2025Article
- Kinetics, Thermodynamics, and Emergence in Stereoediting Reactions.Accounts of chemical research · 2025Article
Corrections and comments
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Authors and funding
7 authors.
Funding
Abstract
Quaternary stereocenters play a crucial role in shaping both the molecular topology of small molecules and the outcome of stereoselective transformations. While considerable progress has been achieved in constructing highly substituted carbon centers with varied substitution patterns, the stereoselective synthesis of quaternary carbon centers remains a significant challenge. Here we report a protocol for the precise manipulation of quaternary stereocenters through epimerization. The critical design element of our ketone α-epimerization process was developing a photoactive imine, which circumvents the numerous deleterious pathways of carbonyl photochemistry. Excitation of this imine with visible light in the presence of a photocatalyst enables reversible C-C bond cleavage and reformation to vary the stereochemistry of the quaternary center. This approach allows us to override intrinsic stereochemical outcomes of C-C bond construction, therefore providing novel tactics for retrosynthetic planning. The broad utility of this protocol was demonstrated by the topological alteration of various classes of carbocyclic scaffolds bearing diverse functional groups.
Identifiers
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.