Parallel kinetic resolution of 2-methoxy and 2-phenoxy-substituted carboxylic acids using a combination of quasi-enantiomeric oxazolidinones

2-Methoxy-2-phenyl acetic acid and 2-phenoxy-2-phenylpropionic acid were resolved by the parallel kinetic resolution of their corresponding pentafluorophenyl active ester using a quasi-enantiomeric combination of lithiated oxazolidinones.

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(4R,2S)-Phenyl-3-phenyl-2-methoxyacetyl-oxazolidin-2-oneC18H17NO4Ee >98%; De >98%[α]D20=-14.4 (c 0.22, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (4R,2S)

(4R,2R)-Phenyl-3-phenyl-2-methoxyacetyl-oxazolidin-2-oneC18H17NO4Ee >98%; De >98%[α]D20=-194.7 (c 0.72, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (4R,2R)

(4S,2R)-Isopropy-3-phenyl-2-methoxyacetyl-oxazolidin-2-oneC15H19NO4Ee >98%; De >98%[α]D20=-10.8 (c 2.71, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (4S,2R)

(4S,2S)-Isopropy-3-phenyl-2-methoxyacetyl-oxazolidin-2-oneC15H19NO4Ee >98%; De >98%[α]D20=+138.0 (c 0.28, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (4S,2S)

(4R,2R)-Phenyl-3-phenoxypropionyl-oxazolidin-2-oneC18H17NO4Ee >98%; De >98%[α]D20=+24.2 (c 0.54, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (4R,2R)

(4R,2S)-Phenyl-3-phenoxypropionyl-oxazolidin-2-oneC18H17NO4Ee >98%; De >98%[α]D20=-171.1 (c 0.54, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (4R,2S)

(4S,2S)-Isopropy-3-phenoxypropionyl-oxazolidin-2-oneC15H19NO4Ee >98%; De >98%[α]D20=+13.4 (c 2.2, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (4S,2S)

(4S,2R)-Isopropy-3-phenoxypropionyl-oxazolidin-2-oneC15H19NO4Ee >98%; De >98%[α]D20=+79.5 (c 2.3, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (4S,2R)

(S)-2-Methoxy-2-phenylacetic acidC9H10O3Ee >98%[α]D20=+141.0 (c 4.7, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)

(R)-Phenoxypropionic acidC9H10O3Ee >98%[α]D20=+23.6 (c 3.6, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R)