58008-76-7

Upstream product

• 930-68-7 cyclohexenone 
• 54972-06-4 3,3-ethylenedioxy-2-methylcyclohexanone 
• 1193-55-1 2-methylcyclohexane-1,3-dione 
• 103990-02-9 1,1:3,3-bis(ethylenedioxy)-2-methylcylcohexane 
• 15681-48-8 lithium dimethylcuprate 
• 58008-75-6 7-Oxa-bicyclo[4.1.0]heptan-2-one oxime 

Relevant academic research and scientific papers

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

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.

Direct asymmetric α-hydroxylation of 2-hydroxymethyl ketones

A direct α-hydroxylation of racemic 2-hydroxymethyl ketones with the Sharpless epoxidation catalyst resulted in α,β-dihydroxy ketones in high ee (up to 97%) and in moderate to good isolated yield (up to 58%).