A New Synthesis of α,β-Unsaturated Carboxylic Esters. The Condensation of Ethyl Lithiotrimethylsilylacetate with Carbonyl Compounds

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概要

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• The key step of the title synthesis involves the conversion of ethyl trimethylsilylacetate to the corresponding enolate, <B>1</B>, by treatment with lithium dicyclohexylamide in tetrahydrofuran at −78 °C. The condensation of <B>1</B> with aldehydes and ketones proceeds smoothly to afford the desired two carbon homologated unsaturated esters in excellent yields. The new process is extended with success to readily-enolizable carbonyl compounds and also to chalcone, which gives no trace of the Michael adduct in the present reaction.

• 公益社団法人 日本化学会の論文

著者

• Taguchi Hiroaki

  Department of Industrial Chemistry, Faculty of Engineering, Kyoto University

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• A New Synthesis of α,β-Unsaturated Carboxylic Esters. The Condensation of Ethyl Lithiotrimethylsilylacetate with Carbonyl Compounds

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