Palladium(0)-Catalyzed SN2′ Displacement on 1-Chloro-1-ethenylcyclopropanes: A Versatile Preparation of Functionally Substituted Methylenecyclopropanes1

Gregory McGaffin; Stefan Michalski; Andreas Stolle; Stefan Bräse; Jacques Salaün; Armin de Meijere

doi:10.1055/s-1992-21413

Synlett 1992; 1992(7): 558-560
DOI: 10.1055/s-1992-21413

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Palladium(0)-Catalyzed S_N2′ Displacement on 1-Chloro-1-ethenylcyclopropanes: A Versatile Preparation of Functionally Substituted Methylenecyclopropanes¹

Gregory McGaffin^* , Stefan Michalski, Andreas Stolle, Stefan Bräse, Jacques Salaün, Armin de Meijere

^*Institut für Organische Chemie der Georg-August-Universität Göttingen, Tammannstraße 2, D-3400 Göttingen, Germany

Abstract

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1-Chloro-1-ethenylcyclopropanes 2, readily prepared with a wide range of substituents on the three-membered ring as well as on the terminal vinylic position, react with dialkyl sodiomalonates under palladium(0) catalysis at or above room temperature to give correspondingly substituted (cyclopropylidenethyl)malonates 3 in good to high yields. A trimethylsilyl substituent as in 2e, especially with a Z-orientation, both enhances the reactivity of the substrate and controls the configuration in the product 3 to be predominantly E.

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