Direct construction of 1,3-diaxial diol derivatives by C-H hydroxylation.
Direct hydroxylation of tertiary C-H bonds for construction of 1,3-diaxial diol derivatives was achieved by devising a new detachable dioxirane precursor containing a trifluoromethyl ketone moiety and ethylene tether. Oxone treatment of the ketones led to the corresponding dioxiranes, enabling hydroxy group installment into cyclohexane and steroid derivatives in a regio- and stereoselective manner through intramolecular oxygen insertion.
Kasuya
Satoshi
S
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Kamijo
Shin
S
Inoue
Masayuki
M
D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D004852:Epoxy Compounds / Q000737:chemistry; D006900:Hydroxylation; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D000438:Alcohols; D004852:Epoxy Compounds; C061799:dioxirane