Reactivity of substituted 3-(diethylphosphonyl)-1-(trialkylsilyl)alka-1,3-dienes: Regioselective epoxidation and cyclopropanation reactions

Stereoselective preparation of α‐silylated α‐quaternary unsaturated aldehydes 2 from variously substituted silylated vinyloxiranes is achieved with the aid of palladium(0) catalysis under smooth experimental conditions. One example of a versatile application of this rearrangement reaction, in the case of the tert‐butyldimethyl(3‐vinyloxiran‐2‐yl)silane derivative 1a, has resulted in one‐pot diastereoselective syntheses of the highly functionalized polysubstituted δ‐lactones 33–39, the reactivity of which has been studied.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

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S_N2′ Reactions between Lithiated Carbon Nucleophiles and Silylated Vinyloxiranes – Effects of Salts and Solvents on the Stereocontrol

Marié

Courillon

Malacrìa

2006

Eur J Org Chem

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α,β-Epoxy-γ,δ-alkenyl)-tert-butyldimethylsilanes 1 display, a priori, three electrophilic centres and two acidic protons. Depending on the configurations of their oxirane rings, the title compounds react towards lithiated bases either through metallation or S N 2Ј reactions. In this paper we demonstrate that the trans-2-(tert-butyldimethylsilyl)-3-vinyloxiran 1a reacts regioselectively with primary, secondary and tertiary butyllithium in S N 2Ј fashion, which allows the formation of α-[a] Université Pierre et Marie Curie, Laboratoire de Chimie Organique, associé au CNRS, FR2769, Tour 44-54 2ème étage, B 229,

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Reactivity of substituted 3-(diethylphosphonyl)-1-(trialkylsilyl)alka-1,3-dienes: Regioselective epoxidation and cyclopropanation reactions

Cited by 6 publications

References 13 publications

ChemInform Abstract: Reactivity of Substituted 3‐(Diethylphosphonyl)‐1‐(trialkylsilyl)alka‐1,3‐dienes: Regioselective Epoxidation and Cyclopropanation Reactions.

ChemInform Abstract: Reactivity of Substituted 3‐(Diethylphosphonyl)‐1‐(trialkylsilyl)alka‐1,3‐dienes: Regioselective Epoxidation and Cyclopropanation Reactions.

Silylated Vinyloxiranes – Recent Advances and Synthetic Applications

S_N2′ Reactions between Lithiated Carbon Nucleophiles and Silylated Vinyloxiranes – Effects of Salts and Solvents on the Stereocontrol

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Reactivity of substituted 3-(diethylphosphonyl)-1-(trialkylsilyl)alka-1,3-dienes: Regioselective epoxidation and cyclopropanation reactions

Cited by 6 publications

References 13 publications

ChemInform Abstract: Reactivity of Substituted 3‐(Diethylphosphonyl)‐1‐(trialkylsilyl)alka‐1,3‐dienes: Regioselective Epoxidation and Cyclopropanation Reactions.

ChemInform Abstract: Reactivity of Substituted 3‐(Diethylphosphonyl)‐1‐(trialkylsilyl)alka‐1,3‐dienes: Regioselective Epoxidation and Cyclopropanation Reactions.

Silylated Vinyloxiranes – Recent Advances and Synthetic Applications

SN2′ Reactions between Lithiated Carbon Nucleophiles and Silylated Vinyloxiranes – Effects of Salts and Solvents on the Stereocontrol

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S_N2′ Reactions between Lithiated Carbon Nucleophiles and Silylated Vinyloxiranes – Effects of Salts and Solvents on the Stereocontrol