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Journal ArticleDOI

Organocatalytic Oxidation. Asymmetric Epoxidation of Olefins Catalyzed by Chiral Ketones and Iminium Salts

O. Andrea Wong, +1 more
- 01 Jul 2008 - 
- Vol. 108, Iss: 9, pp 3958-3987
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.

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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

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

Designing New Chiral Ketone Catalysts. Asymmetric Epoxidation of cis-Olefins and Terminal Olefins

TL;DR: A new class of chiral oxazolidinone ketone catalyst for asymmetric epoxidation with high ee values is described, showing that electronic interactions play an important role in stereodifferentiation.
Journal ArticleDOI

Epoxidation of alkenes by dimethyldioxirane: Evidence for a spiro transition state

TL;DR: The relative reactivity series for the epoxidation of alkenes by dimethyldioxirane showed the reaction to be unexpectedly sensitive to steric factors; cis compounds were ∼8 times as reactive as the trans isomers as mentioned in this paper.
Journal ArticleDOI

Enantioselective epoxidation of terminal olefins by chiral dioxirane.

TL;DR: An enantioselective epoxidation of terminal olefins using chiral ketone 3 as catalyst and Oxone as oxidant and up to 85% ee has been obtained.
Journal ArticleDOI

Catalytic enantioselective epoxidation of alkenes with a tropinone-derived chiral ketone

TL;DR: The α-Fluoro-N-ethoxycarbonyltropinone is an efficient catalyst for the epoxidation of alkenes by Oxone® with good enantioselectivity.
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