Ferrocene Analogues of Hydrogen-Bond-Donor Catalysts: An Investigative Study on Asymmetric Michael Addition of 1,3-Dicarbonyl Compounds to Nitroalkenes

Abstract

This report describes the synthesis of eight ferrocene derivatives of squaramide- or thiourea- based bifunctional catalysts containing cinchona alkaloid moieties. A stepwise sequential route was used to assemble the various components of these ferrocene derivatives. The resulting bifunctional catalysts were used successfully in asymmetric Michael additions of 1,3-dicarbonyl compounds to β-nitrostyrenes. The corresponding products were obtained in high yields and in good to excellent enantioselectivities and diastereoselectivities under mild conditions by using 1 mol% of the catalyst.

Key words

Michael additions - asymmetric catalysis - ferrocenes - alkaloids - nitro compounds - dicarbonyl compounds

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