ArticleACS catalysis2022
Visible Light-Mediated, Diastereoselective Epimerization of Morpholines and Piperazines to More Stable Isomers.
Article in ACS catalysis, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed, 15 citations in OpenAlex.
- Distance-Dependent, Rate-Accelerating and Diastereoselective Directing Effects in Decatungstate-Mediated Stereoediting Reactions.Journal of the American Chemical Society · 2026Article
- Photocatalytic Stereoselective Editing of Alkynes to 3D Molecules via Hydrogen Atom Transfer-Mediated Dynamic Epimerization.Nature communications · 2026Article
- Photocatalytic Synthesis of Substituted 2-Aryl Morpholines via Diastereoselective Annulation.Journal of the American Chemical Society · 2025Article
- Switchable Enantio- and Diastereoselective Michael Additions of β-Keto Amides to Nitroolefins: Crystallization-Based Inversion of Kinetic Stereocontrol.Organic letters · 2024Article
- Copper-Catalyzed Three-Component Synthesis of Highly Substituted Morpholines.Organic letters · 2024Article
- Visible-Light-Mediated, Diastereoselective Epimerization of Exocyclic Amines.Organic letters · 2023Article
- Enantio- and Diastereoselective Mannich Reactions of ß-Dicarbonyls by Second Stage Diastereoconvergent Crystallization.ACS catalysis · 2023Article
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Authors and funding
5 authors at 2 institutions in 1 country.
Funding
Abstract
We report a photocatalyzed epimerization of morpholines and piperazines that proceeds by reversible hydrogen atom transfer (HAT) and provides an efficient strategy for editing the stereochemical configurations of these saturated nitrogen heterocycles, which are prevalent in drugs. The more stable morpholine and piperazine isomers are obtained from the more synthetically accessible but less stable stereoisomers, and a broad scope is demonstrated in terms of substitution patterns and functional group compatibility. The observed distributions of diastereomers correlate well with the relative energies of the diastereomer pairs as determined by density functional theory (DFT) calculations. Mechanistic studies, including luminescence quenching, deuterium labeling reactions, and determination of reversibility support a thiyl radical mediated HAT pathway for the epimerization of morpholines. Investigation of piperazine epimerization established that the mechanism is more complex and led to the development of thiol free conditions for the highly stereoselective epimerization of
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