Synthesis, characterisation and application of enantiomeric isotopomers of Evans’ oxazolidinones

The synthesis of a series of enantiomerically pure deuterium-labelled isotopomeric Evans’ oxazolidinones is discussed.

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(S)-Dideuterio-phenylglycinolC8H9D2NOEe >98%[α]D20=+33.0 (c 0.9, 1 M HCl)Source of chirality: chiral poolAbsolute configuration: (S)

(4S)-4-Phenyl-5,5-dideuterio-oxazolidin-2-oneC9H7D2NO2Ee >98%[α]D20=+48.4 (c 1.0, CHCl3)Source of chirality: chiral poolAbsolute configuration: (S)

(R)-DideuteriovalinolC5H11D2NOEe >98%[α]D20=-13.4 (c 2.4, CHCl3)Source of chirality: chiral poolAbsolute configuration: (R)

(R)-4-Isopropyl-5,5-dideuterio-oxazolidin-2-oneC9H9D2NO2Ee >98%[α]D20=+105.9 (c 2.6, CHCl3)Source of chirality: chiral poolAbsolute configuration: (R)

(R)-Dideuterio-phenylalaninolC9H11D2NOEe >98%[α]D20=+130.4 (c 1.8, CHCl3)Source of chirality: chiral poolAbsolute configuration: (R)

(4R)-4-Benzyl-5,5-dideuterio-oxazolidin-2-oneC10H9D2NO2Ee >98%[α]D20=+53.7 (c 1.0, CHCl3)Source of chirality: chiral poolAbsolute configuration: (R)

(S)-N-tert-Butoxycarbonyl-(4-tert-butyldimethylsilyoxyphenyl)-glycine ethyl esterC21H35NO5SiEe >98%[α]D20=+68.7 (c 12.7, CH2Cl2)Source of chirality: chiral poolAbsolute configuration: (S)

(S)-N-tert-Butoxycarbonyl-(4-tert-butyldimethylsilyoxyphenyl)-dideuterioglycinolC19H31D2NO4SiEe >98%[α]D20=+20.0 (c 38.5, CH2Cl2)Source of chirality: chiral poolAbsolute configuration: (S)

(S)-4-(4-tert-Butyldimethylsilyoxyphenyl)-5,5-dideuterio-oxazolidin-2-oneC15H21D2NO3SiEe >98%[α]D20=+34.5 (c 3.1, DMSO)Source of chirality: chiral poolAbsolute configuration: (S)

(S)-4-(4-Hydroxyphenyl)-5,5-dideuterio-oxazolidin-2-oneC9H7D2NO3Ee >98%[α]D20=+21.6 (c 2.2, DMSO)Source of chirality: chiral poolAbsolute configuration: (S)

(S)-4-Phenyl-5,5-dideuterio-3-benzoyl oxazolidin-2-oneC16H11D2NO3Ee >98%[α]D20=+77.7 (c 0.4, CHCl3)Source of chirality: chiral poolAbsolute configuration: (S)

(R)-4-Phenyl-3-benzoyl oxazolidin-2- oneC16H13NO3Ee >98%[α]D20=-91.8 (c 0.73, CHCl3)Source of chirality: chiral poolAbsolute configuration: (R)

(2S,4R)-4-Phenyl-3-(6-methoxy-(2-naphthyl)propionyl)oxazolidin-2-oneC23H21NO4De >98%; ee >98%[α]D20=+166.2 (c 1.5, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S,R)

(2R,4R)-4-Phenyl-3-(2-phenylbutyryl)oxazolidin-2-oneC19H19NO3De >98%; ee >98%[α]D20=-160.0 (c 0.74, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R,R)

(2S,4S)-4-Phenyl-5,5-dideuterio-3-(2-phenylbutyryl)oxazolidin-2-oneC19H19NO3De >98%; ee >98%[α]D20=-54.2 (c 4.6, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R,S)