77086-44-3

Upstream product

• 930-68-7 cyclohexenone 
• 77086-38-5 ketene t-butyldimethylsilyl methyl acetal 

Downstream Products

• 57026-69-4 methyl (2-methyl-3-oxocyclohexyl)acetate 

Relevant academic research and scientific papers

Carbon-carbon bond formation catalyzed by lithium perchlorate in dichloromethane

A catalytic amount of lithium perchlorate suspended in dichloromethane provides a mild and effective medium for Mukaiyama aldol reactions of aldehydes with silyl ketene acetal (1). 2-Cyclohexenone undergoes clean 1,4-addition under similar conditions. Catalyst activity is much higher in dichloromethane than in diethyl ether.

Highly Effective Catalysts for the Conjugate Addition of Silyl Ketene Acetals to Enones (Mukaiyama-Micael Reaction)

Conjugate additions of O-silylated ketene acetals to simple enones have been reported to proceed without a catalyst if acetonitrile is used as solvent.Inability to repeat this procedure led to the discovery that an as yet unknown species formed from P4O10

Lithium Cobalt-Bis-Dicarbollide: A Novel Lewis Acid Catalyst for the Conjugate Addition of Silyl Ketene Acetals to Hindered α,β-Unsaturated Carbonyl Compounds

The novel Lewis acid, lithium cobalt-bis-carbollide (1), in which the lithium ion is weakly coordinated to the Co(B9C2H11)2(1-) anion, is an effective, soluble catalyst for Mukaiyama-Michael reactions.

Lithium perchlorate catalyzed conjugate addition of O-silylated ketene acetals to hindered α,β-unsaturated carbonyl compounds at atmospheric pressure

O-silylated ketene acetals undergo 1,4 conjugate addition to hindered α,β-unsaturated carbonyl systems at atmospheric pressure in the presence of lithium perchlorate.

Clay Montmorillonite: An Efficient Heterogeneous Catalyst for Michael Reactions of Silyl Ketene Acetals and Silyl Enol Ethers with α,β-Unsaturated Carbonyl Compounds

The Michael addition of silyl ketene acetals to α,β-unsaturated esters (enoates) is investigated.The reaction is catalyzed by clay montmorillonite (solid acid) most effectively among various, homogeneous and heterogeneous acid promoters.The montmorillonite-catalyzed reaction has several prominent features: (1) Not only α- or β-monosubstituted acrylates but also α,β- or β,β-disubstituted acrylates are applicable. (2) The highly regioselective 1,4-addition to a polyenoate is achievable. (3) The michael adduct can be obtained in the form of a labile silyl ketene acetal owing to a simple work-up procedure.The Michael reaction of a silyl enol ether and silyl ketene acetals with α,β-unsaturated ketones (enones) is also described.

Keten Silyl Acetal Chemistry; Simple Synthesis of Methyl Jasmonate and Related Compounds by Utilising Keten Methyl Dimethyl-t-butylsilyl Acetal

Conjugate addition of keten silyl acetals to α,β-unsaturated carbonyl compounds in acetonitrile gave a quantitative yield of the corresponding methyl (3-trialkylsiloxyalk-2-enyl)acetates; subsequent site-specific electrophilic substitution yielded the corresponding 2-substituted 3-(alkoxycarbonylmethyl)alkanones.These novel addition and sequential alkylation reactions could be applied to a simple synthesis of methyl jasmonate, methyl didehydrojasmonate, and methyl dihydrojasmonate.

O-silylated ketene acetal chemistry; β-(alkoxycarbonyl)methyl O-silyl enolates, useful synthons for α-substituted-β-(alkoxycarbonyl)methylalkanones

Conjugate addition of O-silylated ketene acetals 2 to α,β-unsaturated carbonyl compounds 1 in acetonitrile gave quantitative yields of the corresponding β-(alkoxycarbonyl)methyl O-silyl enolates 4. Site specific electrophilic substitutions of 4 yielded th