The first asymmetric α-trifluoromethylthiolation of 2-substituted isoxazolidin-5-ones was developed using Maruoka type N-spiro ammonium catalysts under phase-transfer conditions. The resulting products, containing a trifluoromethylthiolated quaternary chiral carbon, were obtained in moderate to good yields and up to 98:2 enantiomeric ratio. Moreover, the easy N−O bond cleavage provided access to undescribed α-trifluoromethylthio-β-2,2-amino acids, with promising applications in biochemistry and medicinal chemistry.
Asymmetric Synthesis of α‑Trifluoromethylthio-β-Amino Acids under Phase Transfer Catalysis
Capaccio, VitoInvestigation
;Sicignano, MarinaInvestigation
;Della Sala, Giorgio
Conceptualization
;Alemàn, José
Conceptualization
2020
Abstract
The first asymmetric α-trifluoromethylthiolation of 2-substituted isoxazolidin-5-ones was developed using Maruoka type N-spiro ammonium catalysts under phase-transfer conditions. The resulting products, containing a trifluoromethylthiolated quaternary chiral carbon, were obtained in moderate to good yields and up to 98:2 enantiomeric ratio. Moreover, the easy N−O bond cleavage provided access to undescribed α-trifluoromethylthio-β-2,2-amino acids, with promising applications in biochemistry and medicinal chemistry.File in questo prodotto:
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