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2005
Dioxole derivatives
R 0170
Diastereoselective Addition of Silyl Metals to γ-Alkoxy Substituted α,β-UnsaturEsters. — The addition of dimethylphenylsilyllithium to the (Z)-ester (I) pro22- 113 ated
ceeds with high anti selectivity in THF/HMPA, whereas in THF high syn selectivity
can be obtained. The (E)-ester (V) reacts with poor stereocontrol under similar conditions. The behavior of trialkylstannylmetals (VIII) and (X) is also investigated. Tandem
acid catalyzed dioxolane ring opening of products (III) and (IV) followed by γ-hydroxyester ring closure produces diastereomeric lactones. — (KRIEF*, A.; DUMONT, W.;
BAILLIEUL, D.; Tetrahedron Lett. 46 (2005) 6, 951-953; Dep. Chem., Fac. Univ.
Notre Dame de la Paix, B-5000 Namur, Belg.; Eng.) — Mais
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