74930-46-4

Upstream product

• 690-19-7 Allyltrifluorosilane 
• 60277-96-5 2-allyl-2-hydroxycyclohexanone 
• 765-87-7 cyclohexane-1,2-dione 
• 268750-62-5 1,2-diallyl-1,2-cyclohexanediol 
• 74930-48-6 cis-1,2-bis<(trimethylsily)oxy>-1,2-diallylcyclohexane 

Relevant academic research and scientific papers

Highly regio- and stereoselective allylation of α-diketones via the fluorosilicate route

A1lylation of enolizable α-diketones with allyltrifluorosilanes in the presence of triethylamine gave the corresponding tertiary homoallyl alcohols in good yield in a highly regio- and stereospecific manner. The reaction proceeds as diallylation with allyltrifluorosilanes yielding the 1,2-diols with high diastereoselectivity. The more sterically demanding crotyl- and prenyltrifluorosilanes lead exclusively to monoallylated products with the allyl group being added γ-regioselectively. In addition, highly diastereoselective crotylation was observed in the formation of the monoallylated α-hydroxy ketones. Asymmetric α-diketones were generally allylated at the less enolized ketone group except when both diketone and allylsilane were sterically hindered.