Stereoselective synthesis of (1R,2S)-2-amino-1,3-diols from (R)-cyanohydrins |
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Authors: | Franz Effenberger Beate Gutterer Jana Syed |
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Affiliation: | Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, D-70569, Stuttgart, Germany |
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Abstract: | Vinyl substituted (1R,2S)-amino alcohols 5 were obtained by addition of vinyl magnesium bromide to the corresponding cyanohydrin O-trimethylsilyl ethers (R)-2. The O- and N-protected vinyl amino alcohols 6 were ozonized at −78°C in methanol yielding (1R,2S)-2-amino-1,3-diols7 in high enantiomeric and diastereomeric excesses. For purification, compounds 7 in some cases were acetylated to give the derivatives (1R,2S)-8. Racemic 6a was converted by oxidative ozonolysis at −78°C in methanolic NaOH solution to the corresponding methyl N-acetyl-β-hydroxy propanoate 9a. The configuration of (1R,2S)-8a was confirmed by x-ray crystallographic analysis. |
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