53638-19-0

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 533-60-8 cyclohexanone-2-ol 
• 108-94-1 cyclohexanone 
• 6838-67-1 1,2-bis(trimethylsilyloxy)cyclohex-1-ene 
• 6651-36-1 1-(Trimethylsilyloxy)cyclohexene 
• 996-50-9 N,N-diethyl-1,1,1-trimethylsilanamine 

Downstream Products

• 89880-40-0 1-(1-Hydroxy-2-trimethylsilanyloxy-cyclohexyl)-3,4-dimethyl-pent-3-en-2-one 
• 89880-43-3 2-(1,2-Dihydroxy-cyclohexyl)-1-phenyl-ethanone 
• 33158-13-3 2-phenyl-4,5,6,7-tetrahydrobenzofuran 
• 192311-16-3 2-(3,3-bis(ethylthio)propyl)-2-(trimethylsiloxy)cyclohexanone 
• 192311-17-4 2-(3,3-bis(ethylthio)propyl)-2-(trimethylsiloxy)methylenecyclohexane 
• 192311-15-2 2-(3-buten-1-yl)-2-(trimethylsiloxy)cyclohexanone 
• 102675-78-5 [2-Trimethylsilanyloxy-cyclohex-(E)-ylidene]-acetic acid methyl ester 
• 89880-39-7 2-(1-Hydroxy-2-trimethylsilanyloxy-cyclohexyl)-1-phenyl-ethanone 
• 89880-42-2 4-(1-Hydroxy-2-trimethylsilanyloxy-cyclohexyl)-3-oxo-butyric acid ethyl ester 
• 89880-41-1 1'-Hydroxy-2'-trimethylsilanyloxy-bicyclohexyl-2-one 

Relevant academic research and scientific papers

1-Bromo-1-lithioethene: A practical reagent for the efficient preparation of 2-bromo-1-alken-3-ols

(Matrix presented) A reliable preparative-scale synthesis of 1-bromo-1-lithioethene is reported. This reagent undergoes clean 1,2-addition with a range of aldehydes and ketones at -105°C to afford the corresponding 2-bromo-1-alken-3-ols in moderate to excellent yield. Efficient diastereoselective addition to α-siloxy and α-methylcyclohexanones, as well as protected 3-keto furanose sugars, is achieved in the presence of 10 mol% CeBr3. The resulting bromoallylic alcohol adducts have considerable potential as synthetic building blocks.

Prins-pinacol spiroannulations

Lewis acid-promoted cyclizations of methylenecyclohexane siloxy acetals 14, 15, and 21 afford spiro[4.5]decanones 22, 25, and 29 in good yield. In all cases, exclusive pinacol rearrangement of C-1 of the original three- carbon acetal side chain is observed suggesting that pinacol rearrangement of the intermediate 9-decalyl cation occurs more rapidly than conformational equilibration. This selectivity should allow Prins-pinacol spiroannulations to be employed in a predictable fashion to construct stereochemically complex spirocycles.

Sensitized Photooxygenation of Silyl Enol Ethers of Cyclic Ketones

α,β-Unsaturated and α-hydroxy ketones are accessible in prototropic ene-reactions with singlet oxygen by sensitized photooxygenation of cyclic silyl enol ethers and subsequent reduction and solvolysis.In a competing silatropic ene-reaction α-silyloxyketones are formed.Formation of different products depends on ring size, configuration and substitution.At C-6 chirally substituted 2-cyclohexenones are synthesized for the first time by sensitized photooxygenation of chiral silyl enol ethers of optically active starting ketones.

A new, facile synthesis of the 3-methyl-2(5H)-furanoid structural unit from ketones

The 3-methyl-2(5H)-furanoid structural unit is prepared from ketones via 1,4-rearrangement of siloxyalkenes on peroxidation and via oxetene rearrangement of 1-diethylaminopropyne in 53-58% overall yield.