49768-04-9

Upstream product

• 81309-65-1 3-Acetoxy-cyclohex-1-enecarboxylic acid ethyl ester 
• 74-88-4 methyl iodide 
• 1655-07-8 ethyl 2-oxocyclohexane carboxylate 
• 69216-87-1 2-Mesyloxy-1-methyl-1-aethoxycarbonyl-cyclohexan 
• 66088-42-4 ethyl 1-methyl-2-hydroxycyclohexanecarboxylate 
• 66088-37-7 ethyl 1-methyl-2-oxocyclohexancarboxylate 
• 49768-01-6 2-Carboxy-2-methyl-hepten-6-saeureethylester 

Downstream Products

• 6553-85-1 1-methyl-cyclohexanecarboxylic acid ethyl ester 
• 6561-08-6 1-Methyl-1-vinyl-cyclohex-2-en 
• 1315320-24-1 C₁₄H₁₇NO₂ 
• 64326-19-8 rac-1-methylcyclohex-2-ene-1-carboxylic acid 
• 343269-60-3 1-methyl-2-cyclohexene-1-carbonyl chloride 
• 66088-39-9 C₈H₁₄O 
• 22911-31-5 1-methyl-2-cyclohexene-1-carbaldehyde 
• 864870-18-8 (1-methylcyclohex-2-enyl)phenylmethanol 
• 125131-28-4 (1-methylcyclohex-2-en-1-yl)(phenyl)methanone 
• 62075-35-8 (±)-geijerone 
• 114300-64-0 4-methyl-4-vinylcyclohex-2-enone 

Relevant academic research and scientific papers

Metal-free oxyaminations of alkenes using hydroxamic acids

A radical-mediated approach to metal-free alkene oxyamination is described. This method capitalizes on the unique reactivity of the amidoxyl radical in alkene additions to furnish a general difunctionalization using simple diisopropyl azodicarboxylate (DIAD) as a radical trap. This protocol capitalizes on the intramolecular nature of the process, providing single regioisomers in all cases. Difunctionalizations of cyclic alkenes provide trans oxyamination products inaccessible using current methods with high levels of stereoselectivity, complementing cis-selective oxyamination processes.

Reduction-alkylation with organocopper(I) reagents-alkyl halydes: Highly regioselective α-alkylation of γ-acetoxy-α,β-enoates with lithium dibutylcuprate-alkyl halides and difference in the reactivity of electron-deficient olefins with organocopper(I)-Lewis acid reagents

Reaction of γ-acetoxy-α,β-enoates with lithium dialkylcuprate followed by alkyl halides results in the predominant or exclusive formation of α-alkyl-β,γ-enoates in high yields under mild conditions, and a synthetic application to (+-)-α-vetispirene is presented.Treatment of diethyl fumarate and triethoxycarbonylethylene with Bu2CuLi*AlCl3 led to 1,4-addition to give conjugate adducts in high yields.In sharp contrast, diethyl maleate and tetraethoxycarbonylethylene predominantly gave the respective reduction products.Evidence for a presumed dianionic intermediate, based on trapping with some electrophyles, is also presented.Keywords - γ-oxygenated α,β-enoate; β,γ-enoate; deconjugative reduction; α-vetispirene; lithium dialkylcuprate; organocopper(I)-Lewis acid.

Highly Regioselective α-Alkylation of γ-Acetoxy-α,β-enoates by Reduction-Alkylation with Lithium Dibutylcuprate-Alkyl Halide: Application to the Synthesis of Spirovetivanes

Reaction of γ-acetoxy-α,β-enoates with lithium dibutylcuprate followed by alkyl halides results in the predominant or exclusive formation of α-alkyl-β,γ-enoates in high yields under mild conditions; a synthetic route to (+/-)-α-vetispirene is also present