Journal ArticleDOI
Organocatalytic Oxidation. Asymmetric Epoxidation of Olefins Catalyzed by Chiral Ketones and Iminium Salts
O. Andrea Wong,Yian Shi +1 more
TLDR
Ketones with an Attached Chiral Moiety, Chiral Iminium Salt-Catalyzed Epoxidation, and Other Carbohydrate-Based Catalysts 3976 2.8.2.Abstract:
2.6.4. Other Carbohydrate-Based Catalysts 3976 2.7. Carbocyclic Ketones 3977 2.8. Ketones with an Attached Chiral Moiety 3979 3. Chiral Iminium Salt-Catalyzed Epoxidation 3979 3.read more
Citations
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Enzyme-mediated oxidations for the chemist
TL;DR: The present state of the art in the use of enzymes and microorganisms for catalytic oxidation and oxyfunctionalization chemistry is reviewed.
Journal ArticleDOI
Organocatalytic asymmetric epoxidation and aziridination of olefins and their synthetic applications.
Journal ArticleDOI
Recent advances in catalytic asymmetric epoxidation using the environmentally benign oxidant hydrogen peroxide and its derivatives.
TL;DR: A critical review discusses the advances that have been made using both metal-based and organocatalytic homogeneous catalysts to produce epoxides using environmentally benign oxidants, especially hydrogen peroxide.
Journal ArticleDOI
An organocatalytic asymmetric chlorolactonization.
TL;DR: This work represents the first example of an enantioselective reagent-controlled chlorolactonization that approaches synthetically useful enantiOSElectivities.
Journal ArticleDOI
Catalytic Asymmetric Oxygenations with the Environmentally Benign Oxidants H2O2 and O2.
TL;DR: An overview of catalyst systems capable of conducting asymmetric oxygenative transformations of organic molecules and, in line with the major trend to sustainability, relying on green oxidants H2O2 and O2 as the ultimate oxygen source is given.
References
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Journal ArticleDOI
A cyclodextrin-modified ketoester for stereoselective epoxidation of alkenes.
TL;DR: The 2-mediated (S)-alpha-terpineol epoxidations proceeded to give terpineol oxides in high yields, and the stereoselectivities decreased from 2.5:1 to 1:1.2 with increasing steric bulkiness of the terpenes.
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Synthesis of oxepanes and trans-fused bisoxepanes via biomimetic, endo-regioselective tandem oxacyclizations of polyepoxides.
TL;DR: The first examples of tandem endo-regioselective and stereospecific oxacyclizations of 1, 5-diepoxides to oxepane products are described and a mechanism for these biomimetic oxacyClizations is proposed in which the epoxides act as both electrophilic and nucleophilic reaction partners.
Journal ArticleDOI
Isotope effects and the nature of enantioselectivity in the shi epoxidation. The importance of asynchronicity.
Daniel A. Singleton,Zhihong Wang +1 more
TL;DR: The epoxidation of beta-methylstyrene catalyzed by the Shi fructose-derived ketone is studied using experimental kinetic isotope effects and DFT calculations, and the nature of enantioselectivity in this and related epoxidations is considered.
Journal ArticleDOI
Ladder polyether synthesis via epoxide-opening cascades using a disappearing directing group.
TL;DR: The combination of a trimethylsilyl group, a Brønsted base, a fluoride source, and a hydroxylic solvent enables the first construction of the tetrad of tetrahydropyran rings found in the majority of the ladder polyether natural products.
Journal ArticleDOI
Kinetics and mechanism of the oxidation of pyridine by Caro's acid catalyzed by ketones
TL;DR: In this article, the rate law for the pyridine 1-oxide was shown to be -d[Py]/dt = KlK2klkz[Py][HOOSO3-] [OH-][ketone]/(k,[H0OsO3~] + k,'K3[OH]- [HOOSJ + k b [P y ] ).