Helical Amide Derivatives: Synthesis by Insertion of Aliphatic ­Primary Amines into Benzo-Fused 2,2′-Diphenoquinones and Dia­stereomeric Resolution

Abstract

AbstractWe have developed a method for synthesizing novel helical amide derivatives. Nucleophilic primary amines were inserted into benzo-fused 2,2′-biphenoquinones to form helical amides containing seven-membered rings. When optically pure primary amines were used in this reaction, a mixture of two amide diastereoisomers was obtained and separated into diastereomerically pure products by high-performance liquid chromatography. In contrast, the reaction of enantiomerically pure benzo-fused 2,2′-biphenoquinones with achiral aliphatic primary amines afforded enantiomerically pure helical amides with stereospecificity and retention of configuration.