383366-05-0Relevant academic research and scientific papers
Intramolecular ene reaction of epoxyallylsilanes: Synthesis of allyl- and vinylsilane-functionalized cyclohexanols
Barbero, Asuncion,Castreno, Pilar,Fernandez, Gloria,Pulido, Francisco J.
, p. 10747 - 10752 (2007/10/03)
Epoxyallylsilanes bearing the bulky tert-butyldiphenylsilyl group undergo an uncommon tandem rearrangement-cyclization process upon treatment with Lewis acids. Two pathways for the carbonyl ene reaction are observed: one leading to allylsilane-cyclohexano
Intramolecular cyclization of tert-butyldiphenylallylsilane units and carbonyl groups: Allylsilane terminated cyclization versus the ene reaction
Barbero,Castreno,Garcia,Pulido
, p. 7723 - 7728 (2007/10/03)
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.
