title: Conversion of cycloalk-2-enones into 2-methylcycloalkane-1,3-diones--assessment of various Tamao-Fleming procedures and mechanistic insight into the use of the Me3SiMe2Si unit.
abstract: Conjugate addition of Me3SiMe2SiLi to cycloalk-2-en-1-ones, ketalization, Tamao-Fleming oxidation (Bu4NF, then H2O2, KHCO3), TPAP oxidation and acid hydrolysis generates 2-methyl cycloalkane-1,3-diones. Ketalization is needed in order to prevent addition of Me3Si(-) to the carbonyl. The pentamethyldisilanyl group has advantages over other silicon units that are used in Tamao-Fleming procedures.
authors.affiliation: Chemistry Department, University of Alberta, Edmonton, Alberta T6G 2G2, Canada. derrick.clive@ualberta.ca.
authors.forename: Guojun
authors.initials: G
authors.lastname: Yu
authors.affiliation: Chemistry Department, University of Alberta, Edmonton, Alberta T6G 2G2, Canada. derrick.clive@ualberta.ca.
authors.forename: Derrick L J
authors.initials: DL
authors.lastname: Clive