Parallel kinetic resolution of racemic oxazolidinones using quasi-enantiomeric active esters

Racemic Evans’ oxazolidinones were efficiently resolved using a combination of quasi-enantiomeric profens. The levels of stereocontrol were high, leading to products with predictable configurations.

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(4S)-Isopropyl-3-[2S-(6-methoxynaphth-2-yl)-propionyl]-oxazolidin-2-oneC20H23NO4Ee >98%; De >98%[α]D20=+194.3 (c 1.6, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S,S)

(4R)-Isopropyl-3-[2S-(6-methoxynaphth-2-yl)-propionyl]-oxazolidin-2-oneC20H23NO4Ee >98%; De >98%[α]D20=+218.4 (c 2.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S,R)

(4S)-Phenyl-3-[2S-(6-methoxynaphth-2-yl)-propionyl]-oxazolidin-2-oneC23H21NO4Ee >98%; De >98%[α]D20=+167.5 (c 1.4, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S,S)

(4R)-Phenyl-3-[2S-(6-methoxynaphth-2-yl)-propionyl]-oxazolidin-2-oneC23H21NO4Ee >98%; De >98%[α]D20=+59.6 (c 3.3, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S,R)

(4S)-Benzyl-3-[2S-(6-methoxynaphth-2-yl)-propionyl]-oxazolidin-2-oneC24H23NO4Ee >98%; De >98%[α]D20=+135.6 (c 0.73, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S,S)

(4R)-Benzyl-3-[2S-(6-methoxynaphth-2-yl)-propionyl]-oxazolidin-2-oneC24H23NO4Ee >98%; De >98%[α]D20=+29.2 (c 1.2, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S,R)

(4S,5R)-4-Methyl-5-phenyl-3-[2S-(6-methoxynaphth-2-yl)-propionyl]-oxazolidin-2-oneC24H23NO4Ee >98%; De >98%[α]D20=+88.9 (c 1.2, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S,S,R)

(4R,5S)-4-Methyl-5-phenyl-3-[2S-(6-methoxynaphth-2-yl)-propionyl]-oxazolidin-2-oneC24H23NO4Ee >98%; De >98%[α]D20=+142.9 (c 1.4, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S,R,S)

(4R)-Ethyl 2-oxa-3-[2S-(6-methoxynaphth-2-yl)-propionyl]-oxazolidin-4-carboxylateC20H21NO6Ee >98%; De >98%[α]D20=+146.8 (c 0.92, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S,R)

(4S)-Ethyl 2-oxa-3-[2S-(6-methoxynaphth-2-yl)-propionyl]-oxazolidin-4-carboxylateC20H21NO6Ee >98%; De >98%[α]D20=+55.7 (c 3.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S,S)

(4R)-Isopropyl-3-(2R-phenylpropionyl)-oxazolidin-2- oneC15H19NO3Ee >98%; De >98%[α]D20=-109.6 (c 11.6, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R,R)

(4S)-Isopropyl-3-(2R-phenylpropionyl)-oxazolidin-2-oneC15H19NO3Ee >98%; De >98%[α]D20=-19.4 (c 3.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R,S)

(4R)-Phenyl-3-(2R-phenylpropionyl)-oxazolidin-2-oneC18H17NO3Ee >98%; De >98%[α]D20=-179.1 (c 3.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R,R)

(4S)-Phenyl-3-(2R-phenylpropionyl)-oxazolidin-2-oneC18H17NO3Ee >98%; De >98%[α]D20=-83.4 (c 5.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R,S)

(4R)-Benzyl-3-(2R-phenylpropionyl)-oxazolidin-2-oneC19H19NO3Ee >98%; De >98%[α]D20=-104.0 (c 4.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R,R)

(4S)-Benzyl-3-(2R-phenylpropionyl)-oxazolidin-2-oneC19H19NO3Ee >98%; De >98%[α]D20=+1.46 (c9.8, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R,S)

(4R,5S)-4-Methyl-5-phenyl-3-(2R-phenylpropionyl)-oxazolidin-2-oneC19H19NO3Ee >98%; De >98%[α]D20=-39.2 (c 4.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R,R,S)

(4S,5R)-4-Methyl-5-phenyl-3-(2R-phenylpropionyl)-oxazolidin-2-oneC19H19NO3Ee >98%; De >98%[α]D20=-106.9 (c 3.2, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R,S,R)

(4S)-Ethyl 2-oxa-3-(2R-phenylpropionyl)-oxazolidin-4-carboxylateC15H17NO5Ee >98%; De >98%[α]D20=-129.5 (c 2.2, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R,S)

(4R)-Ethyl 2-oxa-3-(2R-phenylpropionyl)-oxazolidin-4-carboxylateC15H17NO5Ee >98%; De >98%[α]D20=-24.8 (c 5.3, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R,R)

(2R)-Pentafluorophenyl 2-(4-isobutylphenyl)propionateC19H17F5O2Ee >98%[α]D20=-91.4(c 5.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R)

(4S)-Ethyl 2-oxa-3-{2R-(4-isobutylphenylpropionyl)}-oxazolidin-4-carboxylateC19H25NO5Ee >98%; De >98%[α]D20=-125.4 (c 12.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R,S)

(4R)-Ethyl 2-oxa-3-{2R-(4-isobutylphenylpropionyl)}-oxazolidin-4-carboxylateC19H25NO5Ee >98%; De >98%[α]D20=-25.2 (c 5.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R,R)

(4R)-Isopropyl-3-{2R-(4-isobutylphenylpropionyl)}-oxazolidin-2-oneC19H27NO3Ee >98%; De >98%[α]D20=-87.5 (c 12.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R,R)

(4S)-Isopropyl-3-{2R-(4-isobutylphenylpropionyl)}-oxazolidin-2-oneC19H27NO3Ee >98%; De >98%[α]D20=-33.0 (c 1.2, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R,S)

(4R)-Phenyl-3-{2R-(4-isobutylphenylpropionyl)}-oxazolidin-2-oneC22H25NO3Ee >98%; De >98%[α]D20=+144.5 (c 7.2, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R,R)

(4S)-Phenyl-3-{2R-(4-isobutylphenylpropionyl)}-oxazolidin-2-oneC22H25NO3Ee >98%; De >98%[α]D20=-114.6 (c 4.2, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R,S)

(S)-2-Phenylpropionyl chlorideC9H9ClOEe >98%[α]D20=+73.2 (c 4.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)

(R)-4-Isopropyl-oxazolidin-2-oneC6H11NO2Ee >98%[α]D20=-14.0 (c 2.4, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R)

(S)-4-Isopropyl-oxazolidin-2-oneC6H11NO2Ee >98%[α]D20=+13.7 (c 3.8, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)

(S)-2-Phenylpropionic acidC9H10O2Ee >98%[α]D20=+71.5 (c 2.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)

(S)-2-(6-Methoxynaphth-2-yl)-propionic acidC4H14O3Ee >98%[α]D20=+65.0 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)

(S)-Pentafluorophenyl 2-(6-methoxynaphth-2-yl)-propionateC20H13F5O3Ee >98%[α]D20=+93.6 (c 5.6, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)

(R)-Pentafluorophenyl 2-phenylpropionateC15H9F5O2Ee >98%[α]D20=-75.0 (c 3.3, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R)