Quinine‐Catalysed Double Michael Addition of Malononitrile to 1,5‐Disubstituted Pentadien‐3‐ones: A Stereoselective Route to Cyclohexanones

Abstract

AbstractThe stereoselective synthesis of 4‐oxo‐2,6‐diaryl‐cyclohexane‐1,1‐dicarbonitriles has been developed through double Michael addition of malononitrile to 1,5‐disubstituted pentadien‐3‐ones catalysed by quinine. This simple cascade process affords cyclohexanones in moderate‐to‐good yields, excellent diastereoselectivity and up to 86 % ee. The isolation of the monoaddition product helps to shed light on thestereochemical outcome of the two‐step process.