ol9b04195_si_001.pdf (5.08 MB)
Asymmetric Synthesis of α‑Trifluoromethylthio-β-Amino Acids under Phase Transfer Catalysis
journal contribution
posted on 2019-12-13, 17:03 authored by Vito Capaccio, Marina Sicignano, Ricardo I. Rodríguez, Giorgio Della Sala, José AlemánThe 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-β2,2-amino acids, with promising applications in biochemistry
and medicinal chemistry.
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Trifluoromethylthioisoxazolidin -5-onesacidMaruoka type Nα- trifluoromethylthiolationaccessapplicationbiochemistry2-bondAsymmetric SynthesisratioenantiomericPhase Transfer Catalysistrifluoromethylthiolated quaternary chiral carbonspiro ammonium catalystsundescribedyield-β-Aminophase-transfer conditions-βcleavageAcid
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