Investigations into the parallel kinetic resolution of 2-phenylpropanoyl chloride using quasi-enantiomeric oxazolidinones

The resolution of 2-phenylpropanoyl chloride using an equimolar combination of quasi-enantiomeric oxazolidinones is discussed. The levels of diastereoselectivity were found to be dependent upon the structural nature of the metallated oxazolidinone, temperature and metal counter-ion.

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(4S)-Isopropyl-3-((2S)-phenylpropionyl)oxazolidin-2-oneC15H19NO3De >98%; ee >98%[α]D20=+128.9 (c 3.5, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S,S)

(4S)-Isopropyl-3-((2R)-phenylpropionyl)oxazolidin-2-oneC15H19NO3De >98%; ee >98%[α]D20=-19.8 (c 3.3, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R,S)

(4R,5S)-4-Methyl-5-phenyl-3-((2R)-phenylpropionyl)oxazolidin-2-oneC19H19NO3De >98%; ee >98%[α]D20=-42.7 (c 3.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R,R,S)

(4R,5S)-4-Methyl-5-phenyl-3-((2S)-phenylpropionyl)oxazolidin-2-oneC19H19NO3De >98%; ee >98%[α]D20=+105.9 (c 2.6, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S,R,S)

(4S)-Benzyl-3-((2S)-phenylpropionyl)oxazolidine-2-oneC15H19NO3De >98%; ee >98%[α]D20=+130.4 (c 1.8, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S,S)

(4S)-Benzyl-3-((2R)-phenylpropionyl)oxazolidine-2-oneC15H19NO3De >98%; ee >98%[α]D20=+2.8 (c 5.5, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R,S)

Ethyl (4S,2R)-2-oxa-3-(2′-phenylpropionyl)oxazolidin-4-carboxylateC15H17NO5De >98%; ee >98%[α]D20=-135.8 (c 4.5, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R,S)

Ethyl (4S,2S)-2-oxa-3-(2′-phenylpropionyl)oxazolidin-4-carboxylateC15H17NO5De >98%; ee >98%[α]D20=+17.2 (c 2.2, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S,S)

(4R,2R)-4-Phenyl-3-(2′-phenylpropionyl)oxazolidin-2-oneC18H17NO3De >98%; ee >98%[α]D20=-180.5 (c 1.5, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R,R)

(4R,2S)-4-Phenyl-3-(2′-phenylpropionyl)oxazolidin-2-oneC15H19NO3De >98%; ee >98%[α]D20=+88.5 (c 4.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S,R)

(2S)-Phenylpropionic acidC9H10O2Ee >98%[α]D20=+71.5 (c 0.6, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)

(2R)-Phenylpropionic acidC9H10O2Ee >98%[α]D20=-71.2 (c 0.6, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R)