Organocatalyzed Asymmetric Conjugate Addition of Cyclic β-Keto Esters to (E)-β-Nitroacrylate Derivatives

Abstract

A diaminomethylenemalononitrile organocatalyst efficiently promoted the asymmetric conjugate addition of cyclic β-keto esters to (E)-β-nitroacrylate derivatives, yielding the corresponding β-nitro esters derivatives with excellent enantioselectivities (up to >99 % ee). This is the first successful example of highly stereoselective conjugate addition of cyclic β-keto esters to (E)-β-nitroacrylate derivatives to obtain anti-isomers.

Keywords: Asymmetric conjugate addition; Cyclic β-keto ester; Organocatalyst; β-nitroacrylate; β2-amino acid.