Efficient stereoselective synthesis of enantiopure 2-substituted paraconic acids

Eight enantiopure (2S,3S)-2-aryl-5-oxotetrahydrofuran-3-carboxylic acids have been synthesized. The key step was a highly stereoselective aldol reaction between an N-acyl oxazolidinone and a corresponding aldehyde.

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(2S,3S)-2-(Benzo[d][1,3]dioxol-5-yl)tetrahydro-5-oxofuran-3-carboxylic acidC12H10O6[α]D25=−44.2 (c 1.0, MeOH)Source of chirality: asymmetric synthesisAbsolute configuration: (2S,3S)

(2S,3S)-Tetrahydro-5-oxo-2-phenylfuran-3-carboxylic acidC11H10O4[α]D25=−37.4 (c 1.0, MeOH)Source of chirality: asymmetric synthesisAbsolute configuration: (2S,3S)

(2S,3S)-Tetrahydro-5-oxo-2-p-tolylfuran-3-carboxylic acidC12H12O4[α]D25=−31.3 (c 1.0, MeOH)Source of chirality: asymmetric synthesisAbsolute configuration: (2S,3S)