Racochote S.Kuhakarn C.Leowanawat P.Chakarawet K.Reutrakul V.Soorukram D.Mahidol University2025-02-262025-02-262025-01-01Asian Journal of Organic Chemistry (2025)https://repository.li.mahidol.ac.th/handle/123456789/105444A practical synthesis of chiral β-trifluoromethyl-β-amino acids is reported by using water as a reaction medium to facilitate the diastereoselective aza-Michael addition of aromatic amines to chiral β-trifluoromethyl-α,β-unsaturated oxazolidinone. A variety of aromatic amines could serve as a suitable nucleophile that readily undergo nucleophilic conjugate addition at ambient temperature to provide the corresponding β-trifluoromethyl-β-amino acid derivatives in excellent combined yields (up to 97 %) with moderate to good diastereoselectivities (up to 3 : 1). Being complementary to the precedent methods, this work offers the advantages, e. g., a green and environmentally friendly reaction medium, a stable and readily synthesized chiral starting material, and a simple and practical operation providing enantioenriched β-trifluoromethyl-β-amino acids which are found major applications in advanced organic synthesis and medicinal research field.ChemistryArticleSCOPUS10.1002/ajoc.2024008122-s2.0-8521816909121935815