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, Vito
Investigation
;
Sicignano, Marina
Investigation
;
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.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11386/4732955
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