One-pot synthesis of enantiomerically pure 1, 2-diols: asymmetric reduction of aromatic α-oxoaldehydes catalysed by Candida parapsilosis ATCC 7330

A facile and simple one-pot method was developed to produce a series of optically active (S)-1-phenyl-1,2-ethanediols with good yields (up to 70%) and high enantiomeric excess (>99%) via asymmetric reduction of various substituted aromatic α-oxoaldehydes using Candida parapsilosis ATCC 7330.

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(S)-(+)-1-Phenyl-1,2-ethanediolC8H10O2ee = 99%[α]D30=+66.9 (c 1.0, CHCl3)Source of chirality: Biocatalytic asymmetric reductionAbsolute configuration: (S)

(S)-(+)-1-(4-Methylphenyl)-1,2-ethanediolC9H12O2ee = >99%[α]D30=+68.5 (c 1.12, CHCl3)Source of chirality: Biocatalytic asymmetric reductionAbsolute configuration: (S)

(S)-(+)-1-(4-Methoxyphenyl)-1,2-ethanediolC9H12O3ee = >99%[α]D30=+60.3 (c 0.50, CHCl3)Source of chirality: Biocatalytic asymmetric reductionAbsolute configuration: (S)

(S)-(+)-1-(3-Methoxyphenyl)-1,2-ethanediolC9H12O3ee = 90%[α]D30=+46.0 (c 1.0, CHCl3)Source of chirality: Biocatalytic asymmetric reductionAbsolute configuration: (S)

(S)-(+)-1-(4-Nitrophenyl)-1,2-ethanediolC8H9NO4ee = 92%[α]D30=+16.5 (c 1.0, MeOH)Source of chirality: Biocatalytic asymmetric reductionAbsolute configuration: (S)

(S)-(+)-1-(3-Nitrophenyl)-1,2-ethanediolC8H9NO4ee = 97%[α]D30=+24.0 (c 1.5, MeOH)Source of chirality: Biocatalytic asymmetric reductionAbsolute configuration: (S)

(S)-(+)-1-(4-Fluorophenyl)-1,2-ethanediolC8H9FO2ee = 97%[α]D30=+62.8 (c 1.0, CHCl3)Source of chirality: Biocatalytic asymmetric reductionAbsolute configuration: (S)

(S)-(+)-1-(4-Chlorophenyl)-1,2-ethanediolC8H9ClO2ee = 99%[α]D30=+52.0 (c 1.60, CHCl3)Source of chirality: Biocatalytic asymmetric reductionAbsolute configuration: (S)

(R)-(-)-1-(2-Chlorophenyl)-1,2-ethanediolC8H9ClO2ee = 62%[α]D30=-43.9 (c 1.90, EtOH)Source of chirality: Biocatalytic asymmetric reductionAbsolute configuration: (R)

(S)-(+)-1-(4-Bromophenyl)-1,2-ethanediolC8H9BrO2ee = >99%[α]D30=+43.4 (c 1.0, CHCl3)Source of chirality: Biocatalytic asymmetric reductionAbsolute configuration: (S)