Asymmetric epoxidation of chromenes mediated by iminium salts: Synthesis of mollugin and (3S,4R)-trans-3,4-dihydroxy-3,4-dihydromollugin

@article{Page2016AsymmetricEO,
  title={Asymmetric epoxidation of chromenes mediated by iminium salts: Synthesis of mollugin and (3S,4R)-trans-3,4-dihydroxy-3,4-dihydromollugin},
  author={Philip C. Bulman Page and Yohan Chan and Abu Hassan Noor Armylisas and Mohammed I. Alahmdi},
  journal={Tetrahedron},
  year={2016},
  volume={72},
  pages={8406-8416}
}

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References

SHOWING 1-10 OF 85 REFERENCES

Asymmetric epoxidation of cis-alkenes mediated by iminium salts: highly enantioselective synthesis of levcromakalim.

[reaction: see text] A range of cis-substituted olefins has been epoxidized with a new dihydroisoquinolinium salt catalyst, using tetraphenylphosphonium monoperoxysulfate as the stoichiometric

Asymmetric epoxidation of olefins catalyzed by chiral iminium salts generated in situ from amines and aldehydes.

A new approach for catalytic asymmetric epoxidation of olefins was developed that utilized chiral iminium salts, generated in situ from chiral amines and aldehydes, as catalysts, which obviates the difficulties inherent in the preparation and isolation of unstable exocyclic imInium salts.

Enantioselective epoxidation of alkenes catalyzed by 2-fluoro-N-carbethoxytropinone and related tropinone derivatives.

Several alpha-substituted N-carbethoxytropinones have been evaluated as catalysts for asymmetric epoxidation of alkenes with Oxone, via a dioxirane intermediate and the alpha-acetoxy derivative 7 affords the highest enantioselectivities.

Asymmetric organocatalytic epoxidations: reactions, scope, mechanisms, and applications.

Recent progress in the development of organocatalytic asymmetric epoxidation methods, the proposed mechanisms of these reactions and their applications as intermediates is reported.

Organocatalytic oxidation. Asymmetric epoxidation of olefins catalyzed by chiral ketones and iminium salts.

Ketones with an Attached Chiral Moiety, Chiral Iminium Salt-Catalyzed Epoxidation, and Other Carbohydrate-Based Catalysts 3976 2.8.2.

Enantioselective olefin epoxidation using novel doubly bridged biphenyl azepines as catalysts

Enantiopure (diastereomeric) doubly bridged biphenyl azepines prepared from (S)-3,3-dimethylbutan-2-amine and (S)-1-phenylpropylamine can be - as a function of the exocyclic side chain - either

Atropo- and Diastereoselective Construction of Tetracyclic Biphenylazepinium Salts Derived from Aminoalcohols: Use as Catalysts in Enantioselective Asymmetric Epoxidation.

A range of new biphenylazepinium salt organocatalysts effective for asymmetric epoxidation has been developed incorporating an additional substituted oxazolidine ring, and providing improved
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