Rh(III)-Catalyzed Ipso and Remote Hydroamidation of Alkenyl Carboxylic Acids to Access Valuable β-Amino Acids

Abstract

β-Amino acids frequently serve as key components in many natural products with significant pharmacological properties and act as precursors to various biologically active compounds. Herein, we present an efficient rhodium-catalyzed ipso and remote hydroamidation of alkenyl carboxylic acids with HBpin and dioxazolones, accessing a series of β-amino acids in good to high yields (up to 96%) with excellent regioselectivity (>20:1 rr). The significance of this transformation is further highlighted by the regioselective process, which enables the synthesis of β-amino acids from isomeric mixtures of alkenyl carboxylic acids. Furthermore, this protocol successfully converts inexpensive and biomass-derived carboxylic acids, such as oleic and elaidic acids, to the corresponding valuable β-amino acids.