ArticleThe Journal of organic chemistry2015
Regio- and Diastereoselective Synthesis of Highly Substituted, Oxygenated Piperidines from Tetrahydropyridines.
Article in The Journal of organic chemistry, 2015. 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.
- Cobalt-catalyzed double hydroboration of pyridines.Chemical science · 2024Article
- The Tungsten-Promoted Synthesis of Piperidyl-ModifiedACS central science · 2023Article
- Modular synthesis of unsaturated aza-heterocycles via copper catalyzed multicomponent cascade reaction.iScience · 2023Article
- Substituted Dihydropyridine Synthesis by Dearomatization of Pyridines.Angewandte Chemie (International ed. in English) · 2021Article
- Rhodium-Catalyzed C-H Alkenylation/Electrocyclization Cascade Provides Dihydropyridines That Serve as Versatile Intermediates to Diverse Nitrogen Heterocycles.Accounts of chemical research · 2021Review
- π-Facial Selectivities in Hydride Reductions of Hindered Endocyclic Iminium Ions.The Journal of organic chemistry · 2019Article
- Catalytic Kinetic Resolution of Disubstituted Piperidines by Enantioselective Acylation: Synthetic Utility and Mechanistic Insights.Journal of the American Chemical Society · 2015Article
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Authors and funding
4 authors.
Funding
Abstract
Diastereoselective epoxidation and regioselective ring-opening methods were developed for the synthesis of densely substituted, oxygenated piperidines from two classes of tetrahydropyridines with distinct stereochemical displays of functionalities. A new and practical in situ prepared epoxidation reagent was developed for the diastereoselective epoxidation of one class of sterically hindered tetrahydropyridines. The novel bifunctional epoxidation reagent, 2-carboperoxy-3,4,5,6-tetrafluorobenzoic acid, was designed to incorporate highly reactive percarboxy acid and pendant carboxylic acid groups, which through hydrogen bonding to the amino group successfully overrode steric effects and directed epoxidation to occur at the more hindered face of the tetrahydropyridine. Nucleophilic ring-opening of the epoxides with water, alcohols, and HF proceeded with high regioselectivity, affording piperidinol products with adjacent tetrasubstituted carbons.
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