Article

Concerning the efficient conversion of epoxy alcohols into epoxy ketones using dioxiranes.

Dipartimento Chimica, Università di Bari, CNR-ICCOM, v. Amendola 173, I-70126 Bari, Italy.
The Journal of Organic Chemistry (impact factor: 4.45). 12/2004; 69(24):8510-3. DOI:10.1021/jo048816w pp.8510-3
Source: PubMed

ABSTRACT Representative epoxy alcohols are cleanly converted into the corresponding epoxy ketones in high yield by selective oxidation using dimethyldioxirane (1a) and its trifluoro analogue (1b) under mild conditions. The oxidation is found to take place leaving the configuration at the epoxy functionality unaffected. The direct oxyfunctionalization of simple cyclic epoxides with the powerful dioxirane 1b provides another attractive method to access epoxy ketones regioselectively.

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Keywords

access epoxy ketones regioselectively
 
attractive method
 
dimethyldioxirane
 
direct oxyfunctionalization
 
epoxy functionality unaffected
 
powerful dioxirane 1b
 
selective oxidation
 
simple cyclic epoxides