37749-87-4Relevant academic research and scientific papers
Lewis Acid-mediated α-Alkoxyalkylation of Carbonyl Compounds Using α-Halo and α-Acetoxy Ethers. - Synthesis of C-Glycosides
Reetz, Manfred T.,Mueller-Starke, H.
, p. 1726 - 1738 (2007/10/02)
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.
