88222-39-3

Upstream product

• 13369-70-5 2-chlorotetrahydrofuran 
• 6651-36-1 1-(Trimethylsilyloxy)cyclohexene 
• 13436-45-8 2-methoxytetrahydrofuran 
• 670-80-4 4-cyclohexen-1-ylmorpholine 
• 1608-67-9 2-acetoxytetrahydrofuran 

Relevant academic research and scientific papers

Reaction of Enamines with Acetals or Trialkyl Orthoformates Activated by Lewis Acids

Enamines, prepared readily from various carbonyl compounds, react with acetals or trialkyl orthoformates in the presence of Lewis acids such as BF3.OEt2 to give corresponding β-alkoxy carbonyl compounds or α-dialkoxymethyl carbonyl compounds in good yields.The reaction of dienamines with acetals or trialkyl orthoformates also selectively gives corresponding β,χ-unsaturated α-(α-alkoxyalkyl) carbonyl compounds or β,χ-unsatureted α-dialkoxymethyl carbonyl compounds in good yields.

Lewis Acid-mediated α-Alkoxyalkylation of Carbonyl Compounds Using α-Halo and α-Acetoxy Ethers. - Synthesis of C-Glycosides

α-Chloro and α-acetoxy ethers such as 2a-b or 4a-b react with silyl enol ethers, O-silylketene acetals, and bis-silylated acyloins in the presence of ZnX2 to form α-alkoxylalkylated carbonyl compounds.The ambident alkylating agent 36 reacts regioselectively at the oxygen-substituted C-atom to afford products such as 39, 41, and 43.The method is mild, regiospecific with respect to isomeric silyl enol ethers and does not afford undesired polyalkylated products.It can be applied in the synthesis of C-glycosides such as 52, 54, and 55.