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Advances in the chemistry of oxaziridines.

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

View Article: PubMed Central - PubMed

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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Target molecules synthesized using oxaziridine-mediatedα-hydroxylation.
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fig4: Target molecules synthesized using oxaziridine-mediatedα-hydroxylation.

Mentions: The oxidationof enolates to α-hydroxycarbonyl compounds is arguably the mostwidely utilized reaction of oxaziridines. The products of these reactionsare valuable intermediates in organic synthesis and key structuralmotifs in many biologically active natural products; several recentlycompleted targets whose syntheses feature oxazirdine-mediated enolateoxidations are featured in Figure 4.93 Prior reviews have detailed early approachesto generating these bonds with facial selectivity utilizing both chiralauxiliaries approaches94 and opticallyactive oxaziridines.95 Much of the contemporaryinterest in this area has focused on catalytic asymmetric α-oxidationsof carbonyl compounds using N-sulfonyloxaziridinesas terminal oxidants.


Advances in the chemistry of oxaziridines.

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

Target molecules synthesized using oxaziridine-mediatedα-hydroxylation.
© Copyright Policy
Related In: Results  -  Collection

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

fig4: Target molecules synthesized using oxaziridine-mediatedα-hydroxylation.
Mentions: The oxidationof enolates to α-hydroxycarbonyl compounds is arguably the mostwidely utilized reaction of oxaziridines. The products of these reactionsare valuable intermediates in organic synthesis and key structuralmotifs in many biologically active natural products; several recentlycompleted targets whose syntheses feature oxazirdine-mediated enolateoxidations are featured in Figure 4.93 Prior reviews have detailed early approachesto generating these bonds with facial selectivity utilizing both chiralauxiliaries approaches94 and opticallyactive oxaziridines.95 Much of the contemporaryinterest in this area has focused on catalytic asymmetric α-oxidationsof carbonyl compounds using N-sulfonyloxaziridinesas terminal oxidants.

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