Axially Chiral 2-Hydroxybiaryls by Palladium-Catalyzed Enantioselective C-H Activation

Abstract

This article describes the discovery and development of a palladium-catalyzed asymmetric C-H olefination of 2-hydroxybiaryls. The strategy allows a direct assembly of optically active, axially chiral 2-substituted-2′-hydroxybiaryls from readily available precursors and demonstrates that the native hydroxy unit of the substrates can work as an efficient directing group for the C-H activation. This represents a substantial advantage over other approaches that require the preinstallation of metal coordinating units. The simplicity of the approach and versatility of the products allow a practical and efficient synthesis of a broad variety of optically active binaphthyl derivatives.