Resolution of pentafluorophenyl 2-phenylpropanoate using combinations of quasi-enantiomeric oxazolidin-2-ones

The kinetic, mutual and parallel resolution of a series of structurally related active esters derived from 2-phenylpropanoic acid using a combination of quasi-enantiomeric oxazolidin-2-ones is discussed.

Figure optionsDownload as PowerPoint slide

(2S,4R)-4-Phenyl-3-(2-phenylpropanoyl)oxazolidin-2-oneC18H17NO3De >98% Ee >98%[α]D20=+128.9 (c 3.5, CHCl3)Source of chirality: chiral poolAbsolute configuration: (S,R)

(2R,4R)-4-Phenyl-3-(2-phenylpropanoyl)oxazolidin-2-oneC18H17NO3De >98% Ee >98%[α]D20=-19.8 (c 3.3, CHCl3)Source of chirality: chiral poolAbsolute configuration: (R,R)

(2R,4S)-4-Isopropyl-3-(2-phenylpropanoyl)oxazolidin-2-oneC15H19NO3De >98% Ee >98%[α]D20=+88.5 (c 5.0, CHCl3)Source of chirality: chiral poolAbsolute configuration: (R,S)

(2S,4S)-4-Isopropyl-3-(2-phenylpropanoyl)oxazolidin-2-oneC15H19NO3De >98% Ee >98%[α]D20=-165.2 (c 2.0, CHCl3)Source of chirality: chiral poolAbsolute configuration: (S,S)

(2R,4S)-4-Benzyl-3-(2-phenylpropanoyl)oxazolidin-2-oneC19H19NO3De >98% Ee >98%[α]D20=+2.8 (c 5.5, CHCl3)Source of chirality: chiral poolAbsolute configuration: (R,S)

(2S,4S)-4-Benzyl-3-(2-phenylpropanoyl)oxazolidin-2-oneC19H19NO3De >98% Ee >98%[α]D20=+130.4 (c 1.8, CHCl3)Source of chirality: chiral poolAbsolute configuration: (S,S)

(2S,4R,5S)-4-Methyl-5-phenyl-3-(2-phenylpropanoyl)oxazolidin-2-oneC19H19NO3De >98% Ee >98%[α]D20=+105.9 (c 2.6, CHCl3)Source of chirality: chiral poolAbsolute configuration: (S,R,S)

(2R,4R,5S)-4-Methyl-5-phenyl-3-(2-phenylpropanoyl)oxazolidin-2-oneC19H19NO3De >98% Ee >98%[α]D20=-42.7 (c 3.0, CHCl3)Source of chirality: chiral poolAbsolute configuration: (R,R,S)

(2S,4S)-Ethyl 2-oxa-3-(2-phenylpropanoyl)oxazolidin-2-oneC15H17NO5De >98% Ee >98%[α]D20=-130.5 (c 2.1, CHCl3)Source of chirality: chiral poolAbsolute configuration: (S,S)

(2R,4S)-Ethyl 2-oxa-3-(2-phenylpropanoyl)oxazolidineC15H17NO5De >98% Ee >98%[α]D20=+24.8 (c 5.3, CHCl3)Source of chirality: chiral poolAbsolute configuration: (R,S)

(2R,4S)-4-Phenyl-3-(2-phenylpropanoyl)oxazolidin-2-thioneC18H17NO2SDe >98% Ee >98%[α]D20=+66.1 (c 3.6, CHCl3)Source of chirality: chiral poolAbsolute configuration: (R,S)

(R)-Pentafluorophenyl 2-phenylpropanoateC15H9F5O2Ee >98%[α]D20=-75.0 (c 3.3, CHCl3)Source of chirality: chiral poolAbsolute configuration: (R)

(R)-4-Methyloxyphenyl 2-phenylpropanoateC16H16O3Ee >98%[α]D20=-103.2 (c 0.5, CHCl3)Source of chirality: chiral poolAbsolute configuration: (R)

(S)-2-Phenylpropanoic acidC9H10O2Ee >98%[α]D20=+69.5 (c 8.2, CHCl3)Source of chirality: chiral poolAbsolute configuration: (S)