50708-48-0

Upstream product

• 110-52-1 1,4-dibromo-butane 
• 632-56-4 tetraethyl ethane-1,1,2,2-tetracarboxylate 
• 6174-95-4 1,1,2,2-tetracarboethoxy-ethylene 

Downstream Products

• 50708-52-6 1,1,2,2-Tetrakis(methansulfonyloxymethyl)cyclohexan 
• 2305-32-0 trans-1,2-cyclohexanedicarboxylic acid 
• 610-09-3 (1R,2S)-cyclohexane-1,2-dicarboxylic acid 
• 50708-50-4 1,1,2,2-Tetrakis(hydroxymethyl)cyclohexan 

Relevant academic research and scientific papers

DIFFERENCES IN THE REACTION OF ELECTRON DEFICIENT OLEFINS WITH ORGANOCOPPER(I)-LEWIS ACID REAGENTS AND EVIDENCE FOR A DIANIONIC EQUIVALENT

Treatment of diethyl fumarate and triethoxycarbonylethylene with Bu2CuLi*AlCl3 led to 1,4-addition to give butylated products in high yields.In sharp contrast, diethyl meleate and tetraethoxycarbonylethylene predominantly gave the respective reduction products.The first evidence for a presumed dianionic intermediate by trapping with some electrophiles was also presented.

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.