Diastereoselective addition of silyl metals to γ-alkoxy substituted α,β-unsaturated esters

A. Krief; W. Dumont; D. Baillieul

doi:10.1016/j.tetlet.2004.12.064

Diastereoselective addition of silyl metals to γ-alkoxy substituted α,β-unsaturated esters

A. Krief, W. Dumont, D. Baillieul

Unite de recherche en chimie organique

Résultats de recherche: Contribution à un journal/une revue › Article › Revue par des pairs

Résumé

Dimethylphenylsilyllithium adds to Z-γ-alkoxy-α,β- unsaturated esters to produce almost exclusively (i) the anti-adducts when the reaction is carried out in THF and (ii) the anti-adduct when carried out in the presence of HMPA. Poor stereocontrol is achieved with stereoisomeric E-γ-alkoxy-α,β-unsaturated esters.

langue originale	Anglais
Pages (de - à)	951-953
Nombre de pages	3
journal	Tetrahedron Letters
Volume	46
Numéro de publication	6
Les DOIs	https://doi.org/10.1016/j.tetlet.2004.12.064
Etat de la publication	Publié - 7 févr. 2005

Accès au document

10.1016/j.tetlet.2004.12.064

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title = "Diastereoselective addition of silyl metals to γ-alkoxy substituted α,β-unsaturated esters",

abstract = "Dimethylphenylsilyllithium adds to Z-γ-alkoxy-α,β- unsaturated esters to produce almost exclusively (i) the anti-adducts when the reaction is carried out in THF and (ii) the anti-adduct when carried out in the presence of HMPA. Poor stereocontrol is achieved with stereoisomeric E-γ-alkoxy-α,β-unsaturated esters.",

author = "A. Krief and W. Dumont and D. Baillieul",

year = "2005",

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journal = "Tetrahedron Letters",

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T1 - Diastereoselective addition of silyl metals to γ-alkoxy substituted α,β-unsaturated esters

AU - Krief, A.

AU - Dumont, W.

AU - Baillieul, D.

PY - 2005/2/7

Y1 - 2005/2/7

N2 - Dimethylphenylsilyllithium adds to Z-γ-alkoxy-α,β- unsaturated esters to produce almost exclusively (i) the anti-adducts when the reaction is carried out in THF and (ii) the anti-adduct when carried out in the presence of HMPA. Poor stereocontrol is achieved with stereoisomeric E-γ-alkoxy-α,β-unsaturated esters.

AB - Dimethylphenylsilyllithium adds to Z-γ-alkoxy-α,β- unsaturated esters to produce almost exclusively (i) the anti-adducts when the reaction is carried out in THF and (ii) the anti-adduct when carried out in the presence of HMPA. Poor stereocontrol is achieved with stereoisomeric E-γ-alkoxy-α,β-unsaturated esters.

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DO - 10.1016/j.tetlet.2004.12.064

M3 - Article

AN - SCOPUS:12344253621

SN - 0040-4039

VL - 46

SP - 951

EP - 953

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 6

ER -

Diastereoselective addition of silyl metals to γ-alkoxy substituted α,β-unsaturated esters

Résumé

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