129065-99-2

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 129065-90-3 (3'S,1R,2S,3R,6S)-2-(3'-((tert-Butyldimethylsilyl)oxy)-3'-cyclohexylprop-1'-ynyl)-3-((tert-butyldimethylsilyl)oxy)bicyclo<4.2.0>octan-7-one 
• 74-88-4 methyl iodide 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 105803-42-7 (3'S,1S,2S,3R,6S)-2-(3'-cyclohexyl-3'-hydroxyprop-1'-ynyl)-3-hydroxybicyclo<4.2.0>octan-7-one 
• 129065-91-4 (3'S,1R,2S,3R,6S)-2-(3'-((tert-Butyldimethylsilyl)oxy)-3'-cyclohexylprop-1'-ynyl)-3-((tert-butyldimethylsilyl)oxy)-6-methylbicyclo<4.2.0>octan-7-one 

Relevant academic research and scientific papers

Enolate Reactions of Bicyclooctan-7-ones

Under kinetic conditions, the lithium enolate formed from the bicyclooctan-7-one 3 undergoes reaction with MeI, EtI, and dimethyl disulfide to give 6-substituted compounds 7-9 in 65percent, 43percent, and 70percent yield, respectively, rather than the anticipated 8-substituted isomers.Similarly, fluorination of the silyl enol ether gives the 6-fluoro compound 10 in 40percent yield.Using a TMSCl trapping technique it was shown that kinetic deprotonation takes place at both the 6- and 8-positions in bicyclooctan-7-ones, whereas the thermodynamic product is the expected 6-enolate.Generation of the enolate from a mixture of 6- and 7-silyl enol ethers (57:43) results in 6- and 8-alkylated products.The kinetic enolate from bicyclooct-2-en-7-one is the 7-enol derivative.