Mukaiyama aldol and Michael reactions catalyzed by lanthanide iodides

Article abstract of DOI:10.1016/S0040-4020(98)00791-1

Samarium diiodide is an efficient catalyst precursor which allows the formation of condensation products between various carbonyl compounds and ketene silyl acetals or enoxysilanes. With α,β-unsaturated carbonyl compounds, 1,2- or 1,4-additions are observed according to the structure of the substrate. α,β-Unsaturated ketones yield to enoxysilanes by selective Michael additions. Aldol products are isolated as silyl ethers. The mechanisms of the reactions are discussed.