Probing the parallel kinetic resolution of 1-phenylethanol using quasi-enantiomeric oxazolidinone adducts

The parallel kinetic resolution of racemic 1-phenylethanol using an equimolar combination of quasi-enantiomeric oxazolidinones is discussed. The levels of diastereoselectivity were high leading to separable quasi-enantiomeric esters in good yield.

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1-Phenylethyl-2-phenylpropionateC17H18O2Ee >98%; De >98%[α]D20=+10.5 (c 3.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R,R)

1-Phenylethyl-2-phenylpropionateC17H18O2Ee >98%; De >98%[α]D20=-60.4 (c 1.9, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R,S)

1-Phenylethyl-2-(6-methoxy-naphthalene-2-yl)propionateC22H22O3Ee >98%; De >98%[α]D20=+26.6 (c 3.2, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S,S)

1-Phenylethyl-2-(6-methoxy-naphthalene-2-yl)propionateC22H22O3Ee >98%; De >98%[α]D20=+8.75 (c 1.64, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S,R)

Di-(1-phenylethyl)-carbonateC17H18O3Ee >98%; De >98%[α]D20=+116.6 (c 0.8, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R,R)

1-Phenylethyl-2-phenylbutyrateC18H20O2Ee >98%; De >98%[α]D20=-12.9 (c 6.2, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S,S)

1-Phenylethyl-2-phenylbutyrateC18H20O2Ee >98%; De >98%[α]D20=+56.4 (c 1.95, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S,R)

1-Phenylethyl 2-(4-isopropylphenyl)propionateC21H26O2Ee >98%; De >98%[α]D20=-14.2 (c 9.8, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R,R)

1-Phenylethyl 2-(4-isopropylphenyl)propionateC21H26O2Ee >98%; De >98%[α]D20=+29.4 (c 0.65, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S,R)

1-PhenylethanolC8H10OEe >95%[α]D20=-43.0 (c 11.4, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)

2-(6-Methoxy-2-naphthyl)propanolC14H16O2Ee >95%[α]D20=-17.7 (c 22.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)

2-(4-Isobutylphenyl)propanolC13H20OEe >95%[α]D20=+18.5 (c 1.6, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R)