Palladium-Catalyzed Ring Opening of Cyclopropane-Appended Spirotricyclic Olefins with Soft Nucleophiles and Organoboronic Acids: Facile Synthesis of Functionalized Spiro[2.4]heptenes

Abstract

The palladium-catalyzed ring opening of cyclopropane- and vinylcyclopropane-appended spirotricyclic olefins by employing active methylene compounds, phenols and organoboronic acids is discussed in detail. The present strategy provides a facile route for the synthesis of biologically significant, functionalized spiro[2.4]heptenes under mild reaction conditions. The synthetic utility of the described compounds is emphasized by the preparation of the corresponding iodolactone derivatives and a highly substituted spiro[2.4]heptane.

Key words

spirotricyclic olefins - spiro[2.4]heptenes - palladium - phenols - boronic acids

• References

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