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

Org Lett

Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, P. R. China.

Published: August 2025


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Article 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.

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http://dx.doi.org/10.1021/acs.orglett.5c02423DOI Listing

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