Introduction of Electrophiles to the α-Position of α,β-Unsaturated Aldehydes and Ketones by Sequential Conjugate Aminosilylation-Alkylation-Deamination

Abstract

Abstract Silylamines add to α,β-unsaturated aldehydes and ketones in 1,4-addition mode to generate amino-substituted silyl enol ethers without any catalysts. These easily isolable silyl enol ethers react with acetals and aldehydes in the presence of a Lewis acid to give α-alkoxyalkyl and α-hydroxyalkyl substituted α,β-unsaturated carbonyl compounds, respectively, after deamination by treatment with silica gel.