Tetrahedron p. 13129 - 13148 (1998)
Update date:2022-08-05
Topics:
Giuseppone, Nicolas
Van De Weghe, Pierre V.
Mellah, Mohamed
Collin, Jacqueline
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.
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