Concerning the efficient conversion of epoxy alcohols into epoxy ketones using dioxiranes.
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.
D'Accolti
Lucia
L
Dipartimento Chimica, Università di Bari, CNR-ICCOM, v. Amendola 173, I-70126 Bari, Italy.
Fusco
Caterina
C
Annese
Cosimo
C
Rella
Maria R
MR
Turteltaub
Joanna S
JS
Williard
Paul G
PG
Curci
Ruggero
R
D000438:Alcohols / Q000138:chemical synthesis / Q000737:chemistry*; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis*; D008968:Molecular Conformation
D000438:Alcohols; D004852:Epoxy Compounds; D007659:Ketones; C061799:dioxirane