Organocatalytic Michael Addition of Naphthoquinone with α,β‐Unsaturated Ketones: Primary Amine Catalyzed Asymmetric Synthesis of Lapachol Analogues

Abstract

Abstract A highly efficient organocatalytic synthesis of lapachol analogues from the Michael addition of naphthoquinone to various α,β‐unsaturated ketones catalyzed by primary amines is presented. Good to high yields (up to 93 %) and high to excellent enantioselectivities (up to 98 % ee ) were obtained for the target compounds. MS (ESI) provided evidence for the key intermediates in the proposed mechanism.