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

Unit of organic chemistry

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	951-953
Number of pages	3
Journal	Tetrahedron Letters
Volume	46
Issue number	6
DOIs	https://doi.org/10.1016/j.tetlet.2004.12.064
Publication status	Published - 7 Feb 2005

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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",

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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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U2 - 10.1016/j.tetlet.2004.12.064

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

Abstract

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