383366-08-3Relevant academic research and scientific papers
Intramolecular cyclization of tert-butyldiphenylallylsilane units and carbonyl groups: Allylsilane terminated cyclization versus the ene reaction
Barbero,Castreno,Garcia,Pulido
, p. 7723 - 7728 (2001)
tert-Butyldiphenylsilylcopper reacts with allene to give an allylsilane-vinylcopper intermediate which upon treatment with α,β-unsaturated ketones leads to allylsilane containing ketones resulting from conjugate addition. These oxoallylsilanes bearing the bulky tert-butyldiphenylsilyl group undergo highly selective intramolecular cyclizations when treated with Lewis acid affording unsaturated cyclopentanols. Two reactivity patterns are observed: allylsilane terminated cyclization involving elimination of silicon or an ene reaction without losing the silyl group. The pathway depends on the ability of a hydrogen β to the carbonyl to be removed in an ene-type process, α,β-Unsaturated acid chlorides lead to silylated cyclopentenones.
