Synthesis of Chiral β-Trifluoromethyl-β-Amino Acid Derivatives in Aqueous Medium
Issued Date
2025-01-01
Resource Type
eISSN
21935815
Scopus ID
2-s2.0-85218169091
Journal Title
Asian Journal of Organic Chemistry
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SCOPUS
Bibliographic Citation
Asian Journal of Organic Chemistry (2025)
Suggested Citation
Racochote S., Kuhakarn C., Leowanawat P., Chakarawet K., Reutrakul V., Soorukram D. Synthesis of Chiral β-Trifluoromethyl-β-Amino Acid Derivatives in Aqueous Medium. Asian Journal of Organic Chemistry (2025). doi:10.1002/ajoc.202400812 Retrieved from: https://repository.li.mahidol.ac.th/handle/123456789/105444
Title
Synthesis of Chiral β-Trifluoromethyl-β-Amino Acid Derivatives in Aqueous Medium
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Abstract
A 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.