An enantiopure galactose oxidase model: synthesis of chiral amino alcohols through oxidative kinetic resolution catalyzed by a chiral copper complex

An enantiopure galactose oxidase (GO) enzyme model has been synthesized from readily available (R)-BINAM and Cu(OTf)2, and the enantiopure GO model has been effectively used in situ as an efficient chiral catalyst for the synthesis of chiral amino alcohols through oxidative kinetic resolution (OKR), where molecular oxygen is used as the sole oxidant. Under the proposed catalytic conditions, both ortho- and para-substituted amino alcohols were resolved with good to excellent enantiomeric excesses through oxidative kinetic resolution.

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(S)-1-(2-Aminophenyl)ethanolC8H11NOEe = 93%[α]D20=+52.5 (c 1.0, CHCl3)Source of chirality: oxidative kinetic resolutionAbsolute configuration: (S)

(S)-(2-Aminophenyl)(phenyl)methanolC13H13NOEe = 87%[α]D25=+44.5 (c 1.0, MeOH)Source of chirality: oxidative kinetic resolutionAbsolute configuration: (S)

(S)-(4-Aminophenyl)(phenyl)methanolC13H13NOEe = 71%[α]D20=-27.5 (c 1.0, MeOH)Source of chirality: oxidative kinetic resolutionAbsolute configuration: (S)