Palladium Hydroxide Catalyzed Transformation of Primary Propargylic Alcohols into Aldehydes: Application to the Synthesis of the Tetrahydrofuran Core

Abstract

A palladium-catalyzed one-pot, two-step sequence involving redox isomerization/reduction of primary propargylic alcohols into the corresponding aldehydes has been achieved at room temperature for the first time in good to excellent yields under mild conditions. The functional group compatibility in this reaction is studied and this new methodology has been successfully applied in the synthesis of the 2,5-trans-tetrahydrofuran ring system of amphidinolides. It is noteworthy that aromatic substituted propargylic alcohols gave a mixture of unsaturated and saturated aldehydes, whereas aliphatic propargylic alcohols gave only saturated aldehydes.

Key words

palladium - alkynes - aldehydes - tetrahydrofuran - one-pot reactions

• References

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