Simple Synthesis of Tetrahydrofurans via Reaction of Enolates of γ-Chloroketones with Aldehydes

Micha Barbasiewicz; Mieczysaw Mąkosza

doi:10.1055/s-2006-926387

PAPER

Simple Synthesis of Tetrahydrofurans via Reaction of Enolates of γ-Chloroketones with Aldehydes

Micha Barbasiewicz, Mieczysaw Mąkosza*
Institute of Organic Chemistry, Polish Academy of Sciences, ul. Kasprzaka 44/52, P.O. Box 58, 01-224 Warsaw 42, Poland
Fax: +48(22)6326681; e-Mail: icho-s@icho.edu.pl;

Abstract

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Abstract

Enolates of γ-chloropropyl ketones react with aldehydes in protic media to form aldol type adducts that cyclize to substituted tetrahydrofurans, whereas in aprotic media they react mainly along an intramolecular substitution pathway giving cyclopropyl ketones. A substantial increase in the nucleophilicity of the enolates and the electrophilicity of aldehydes favors the formation of tetrahydrofurans.

Key words

aldol reactions - enolates - halocarbanions - ketones - tetrahydrofurans

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References

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