Enantiomerically pure allylic alcohols: preparation by Candida parapsilosis ATCC 7330 mediated deracemisation

Biocatalytic deracemisation of racemic allylic alcohols by whole cells of Candida parapsilosis ATCC 7330 resulted in the formation of the (R)-enantiomers in high enantiomeric excesses (up to >99%) and isolated yields (up to 79%).

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(2R,3E)-4-Phenylbut-3-en-2olC10H12OEe >99%[α]D25=+33.2 (c 1.02, CHCl3)Source of chirality: deracemisationAbsolute configuration: (R)

(2R,3E)-4-p-Tolylbut-3-en-2olC11H14OEe = 98%[α]D25=+20.9 (c 0.8, CHCl3)Source of chirality: deracemisationAbsolute configuration: (R)

(2R,3E)-4-o-Tolylbut-3-en-2olC11H14OEe = 95%[α]D25=+15.4 (c 1.1, CHCl3)Source of chirality: deracemisationAbsolute configuration: (R)

(2R,3E)-4-(p-Methoxyphenyl)but-3-en-2olC11H14O2Ee >99%[α]D25=+9.4 (c 1.1, CHCl3)Source of chirality: deracemisationAbsolute configuration: (R)

(2R,3E)-4-(o-Methoxyphenyl)but-3-en-2olC11H14O2Ee = 94%[α]D25=+6.4 (c 1.02, CHCl3)Source of chirality: deracemisationAbsolute configuration: (R)

(2R,3E)-4-(p-Chlorophenyl)but-3-en-2olC10H11ClOEe >99%[α]D25=+28.1 (c 1.02, CHCl3)Source of chirality: deracemisationAbsolute configuration: (R)

(2R,3E)-4-(o-Chlorophenyl)but-3-en-2olC10H11ClOEe = 92%[α]D25=+8.3 (c 0.70, CHCl3)Source of chirality: deracemisationAbsolute configuration: (R)

(2R,3E)-4-(o,p-Dichlorophenyl)but-3-en-2olC10H10Cl2OEe = 90%[α]D25=+4.6 (c 0.50, CHCl3)Source of chirality: deracemisationAbsolute configuration: (R)

(2R,3E)-4-(Naphthlen-1-yl)but-3-en-2olC14H14OEe = 76%[α]D25=+7.2 (c 2.0, CHCl3)Source of chirality: deracemisationAbsolute configuration: (R)