Two-Carbon Homologation of Aldehydes via Silyl Ketene Acetals:  A New Stereoselective Approach to (E)-Alkenoic Acids

Two-Carbon Homologation of Aldehydes via Silyl Ketene Acetals:  A New Stereoselective Approach to (E)-Alkenoic Acids

Aldehydes are converted into (E)-α,β-unsaturated carboxylic acids using C,O,O-tris(trimethylsilyl)ketene acetal 1. This organosilicon reagent is easily generated from trimethylsilyl acetate, LDA, and chlorotrimethylsilane. The effectiveness of the reaction has been explored for a large variety of al...

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Veröffentlicht in:Journal of organic chemistry 1998-11, Vol.63 (24), p.8785-8789
Hauptverfasser: Bellassoued, Moncef, Lensen, Nathalie, Bakasse, Mina, Mouelhi, Sinda
Format: Artikel
Sprache:eng
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Zusammenfassung:Aldehydes are converted into (E)-α,β-unsaturated carboxylic acids using C,O,O-tris(trimethylsilyl)ketene acetal 1. This organosilicon reagent is easily generated from trimethylsilyl acetate, LDA, and chlorotrimethylsilane. The effectiveness of the reaction has been explored for a large variety of aldehydes with Lewis acids and fluorides as catalysts.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo980853y