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Advances in the chemistry of oxaziridines.

Williamson KS, Michaelis DJ, Yoon TP - Chem. Rev. (2014)

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Affiliation: Department of Chemistry, University of Wisconsin-Madison , 1101 University Avenue, Madison, Wisconsin 53706, United States.

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reagents; oxidations and aminations of alkanes, alkenes, arenes, amines, identity of their N-substituent, which exerts a significant effect on their reactivity... and acid, only the tert-butyldiphenylsilyl (TBDPS) derivative has been successfully synthesized... in oxygen transfer reactions to alkenes... tend to be more powerful oxygen atom-transfer reagents, these positively asymmetric epoxidation reactions with moderate to excellent enantioselectivities the α-alcohol after ring-opening of the epoxide... Directed reduction for decomposition of the oxaziridine... Thus, one-electron reduction invoked in Scheme 28... The greater reactivity oxygen atom transfer reactions continues to be the most broadly appreciated

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Representative oxidizing heterocycles with two electrophilicheteroatomswithin a three-membered ring.
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fig1: Representative oxidizing heterocycles with two electrophilicheteroatomswithin a three-membered ring.

Mentions: Oxaziridinesconstitute a subset of a class of versatile oxidantswhose characteristic feature is the presence of two electronegativeheteroatoms within a strained three-membered ring (Figure 1). Other small organic heterocycles in this classinclude diaziridines1 and dioxiranes,2 which have been developed as reagents for a varietyof oxidative transformations. η2-Peroxo and η2-hydroperoxy complexes of various transition metals are alsomembers of this class,3 and these structuresare the active oxidizing species in a broad range of syntheticallyuseful oxidative transformations, including the Sharpless asymmetricepoxidation,4 VO(acac)2-catalyzedepoxidations,5 and MeReO3-catalyzedhydroxylation of unactivated alkanes.6 Peroxometalcomplexes are relevant in biological systems as well; dinuclear μ-η2:η2-peroxodicopper(II) complexes found withinthe active sites of metalloenzymes such as hemocyanin and tyrosinasehave been extensively studied for their role in oxygen metabolism.7


Advances in the chemistry of oxaziridines.

Williamson KS, Michaelis DJ, Yoon TP - Chem. Rev. (2014)

Representative oxidizing heterocycles with two electrophilicheteroatomswithin a three-membered ring.
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4150611&req=5

fig1: Representative oxidizing heterocycles with two electrophilicheteroatomswithin a three-membered ring.
Mentions: Oxaziridinesconstitute a subset of a class of versatile oxidantswhose characteristic feature is the presence of two electronegativeheteroatoms within a strained three-membered ring (Figure 1). Other small organic heterocycles in this classinclude diaziridines1 and dioxiranes,2 which have been developed as reagents for a varietyof oxidative transformations. η2-Peroxo and η2-hydroperoxy complexes of various transition metals are alsomembers of this class,3 and these structuresare the active oxidizing species in a broad range of syntheticallyuseful oxidative transformations, including the Sharpless asymmetricepoxidation,4 VO(acac)2-catalyzedepoxidations,5 and MeReO3-catalyzedhydroxylation of unactivated alkanes.6 Peroxometalcomplexes are relevant in biological systems as well; dinuclear μ-η2:η2-peroxodicopper(II) complexes found withinthe active sites of metalloenzymes such as hemocyanin and tyrosinasehave been extensively studied for their role in oxygen metabolism.7

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, University of Wisconsin-Madison , 1101 University Avenue, Madison, Wisconsin 53706, United States.

AUTOMATICALLY GENERATED EXCERPT
Please rate it.

reagents; oxidations and aminations of alkanes, alkenes, arenes, amines, identity of their N-substituent, which exerts a significant effect on their reactivity... and acid, only the tert-butyldiphenylsilyl (TBDPS) derivative has been successfully synthesized... in oxygen transfer reactions to alkenes... tend to be more powerful oxygen atom-transfer reagents, these positively asymmetric epoxidation reactions with moderate to excellent enantioselectivities the α-alcohol after ring-opening of the epoxide... Directed reduction for decomposition of the oxaziridine... Thus, one-electron reduction invoked in Scheme 28... The greater reactivity oxygen atom transfer reactions continues to be the most broadly appreciated

Show MeSH