67263-00-7

Upstream product

• 1193-18-6 3-methylcyclohexen-2-one 
• 3839-31-4 dimethyl(phenyl)silyllithium 
• 1145-98-8 1,2-diphenyltetramethyldisilane 

Downstream Products

• 1193-18-6 3-methylcyclohexen-2-one 
• 245657-53-8 Trifluoro-methanesulfonic acid 5-(dimethyl-phenyl-silanyl)-5-methyl-cyclohex-1-enyl ester 
• 67262-99-1 3-Methyl-3-trimethylsilanyl-cyclohexanone 
• 80256-12-8 3-dimethyl(phenyl)silyl-2-allyl-3-methylcyclohexanone 
• 67473-42-1 2,3-dimethyl-3-dimethyl(phenyl)silylcyclohexanone 
• 1122-20-9 2,3-dimethylcyclohex-2-en-1-one 
• 245657-67-4 9-((2R,4R,5S,6R)-4,5-Dihydroxy-6-methyl-tetrahydro-pyran-2-yl)-3-(dimethyl-phenyl-silanyl)-8-hydroxy-3-methyl-1,2,3,4-tetrahydro-benzo[a]anthracene-7,12-dione 
• 245657-04-9 Dimethyl-[1-methyl-3-((E)-2-phenylsulfanyl-vinyl)-cyclohex-3-enyl]-phenyl-silane 
• 245657-62-9 1-[5-(Dimethyl-phenyl-silanyl)-5-methyl-cyclohex-1-enyl]-ethane-1,2-diol 
• 245657-65-2 5-(Dimethyl-phenyl-silanyl)-5-methyl-cyclohex-1-enecarbaldehyde 
• 159692-35-0 (+/-)-5-(dimethylphenylsilanyl)-5-methyl-1-vinyl-1-cyclohexene 

Relevant academic research and scientific papers

Conjugate additions of a simple monosilylcopper reagent with use of the CuI-DMS complex: Stereoselectivities and a dramatic impact by DMS

(Chemical Equation Presented) Conjugate additions utilizing the simple monosilylcuprate reagent Li[PhMe2SiCuI] to α,β-unsaturated carbonyl compounds are described. The presence of dimethyl sulfide (DMS), either as a component originating from t

Conjugate addition of dimethylphenylsilyllithium to α,β-unsaturated carbonyl compounds mediated by sub-stoichiometric quantities of dimethylzinc

Dimethylphenylsilyllithium undergoes conjugate addition to a variety of α,β-unsaturated enones in the presence of sub-stoichiometric amounts of dimethylzinc. Down to 10 mol % of Me2Zn facilitates these reactions to afford good to excellent yields of β-silylated products. This catalytic behavior is displayed when the Me2Zn used is generated in situ, from the addition of methyllithium to zinc (II) iodide or when used directly from a commercial source. This methodology in which sub-stoichiometric quantities of the reactive organometallic reagent are present at a given time may provide a route for catalytic enantioselective conjugate addition of trialkylsilyl moieties to enones.

Total synthesis of urdamycinone B via C-glycosidation of an unprotected sugar and Diels-Alder reaction of C-glycosyl juglone

The total synthesis of C-glycosyl angucycline, urdamycinone B 1, was achieved via C-glycosidation of naphthol 6 and the unprotected D-olivose 7, and Diels-Alder reaction of the unprotected C-glycosyl juglone 9 and the diene 17 as the key steps.

Observations on Various Silyl-Cuprate Reagents

The mixed silyl-cuprate reagent (6), made from 1 equiv. of methyl-lithium, 1 equiv. of phenyldimethylsilyl-lithium, and 1 equiv. of copper(I) cyanide, reacts with 3-methylcyclohexenone (7), with methyl cinnamate (9), with 1-vinylcyclohexyl acetate (11), a

The Conjugate Addition of a Silyl Group to Enones and its Removal with Copper(II) Bromide: A Protecting Group for the αβ-Unsaturation of αβ-Unsaturated Ketones

Silyl-lithium reagents mixed with copper(I) salts react with enones, including esters and aldehydes, to give β-silyl carbonyl compounds in good yield.The β-silylketones can be used in synthesis without risk to the silyl group and the enone group can be restored by bromination-desilylbromination with copper(II) bromide.The principle is illustrated with syntheses of carvone and dihydrojasmone.