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

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

References

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