The easy chromatographic separation of the diastereomeric mixture of oxaxolidin-2-onesls and s allows to synthesize pure R-(-j-& and (S)-(+)-GABOB lb. The H NMR pattern of 2 and 5 can be correlated with the configuration at C-5 and this relationship is confirmed by MM2 calculations for rotamers of 5
Synthesis of both enantiomers of 4-vinyl oxazolidin-2-one from a single precursor: D-isoascorbic acid
β Scribed by Giuliano Delle Monache; Domenico Misiti; Patrizia Salvatore; Giovanni Zappia
- Publisher
- John Wiley and Sons
- Year
- 2000
- Tongue
- English
- Weight
- 122 KB
- Volume
- 12
- Category
- Article
- ISSN
- 0899-0042
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β¦ Synopsis
A convenient synthesis of (S)-and (R)-4-vinyl oxazolidin-2-one 1 and 2 from the same inexpensive starting material, D-isoascorbic acid, is described. The title compounds were obtained in 44% and 38% yield, respectively, by operationally simple steps. This approach is a suitable alternative to the literature methods and enhances the synthetic utility of these intermediates.
π SIMILAR VOLUMES
Starting from ornithine, an efficient scalable one-pot 3-step procedure for the synthesis of the enantiopure bromo acid (I) is reported. It can be easily converted to chiral benzoylsulfanyl derivative (III), an intermediate in the synthesis of MMP inhibitors. -(HOLT, K.
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