Tetrahedron Asymmetry p. 2933 - 2944 (1995)
Update date:2022-08-02
Topics:
Effenberger, Franz
Gutterer, Beate
Syed, Jana
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 deg C in methanol yielding (1R,2S)-2-amino-1,3-diols 7 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 deg 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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