Highly Enantioselective Michael Addition of Aromatic Ketones to Nitrodienes and the Application to the Synthesis of Chiral γ-Aminobutyric Acid

Abstract

A highly enantioselective Michael addition of aromatic ketones to α,β,γ,δ-unsaturated nitro compounds is described. In the presence of a chiral primary amine-thiourea based on dehydroabietic amine, γ-nitro ketones were obtained in excellent enantioselectivities (up to 95% ee) with up to 95% yield. In addition, this methodology has been successfully applied in the asymmetric synthesis of chiral 3-(aminomethyl)-5-phenylpentanoic acid.

Key words

chiral primary amine-thiourea - enantioselective catalysis - ketone - Michael addition - nitrodiene

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