Stereoselective synthesis of (1 R,2 S)-2-amino-1,3-diols from ( R)-cyanohydrins

Vinyl substituted (1 R,2 S)-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 (1 R,2 S)-2-amino-1,3-diols 7 in high enantiom...

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Bibliographic Details
Published inTetrahedron: asymmetry Vol. 6; no. 12; pp. 2933 - 2943
Main Authors Effenberger, Franz, Gutterer, Beate, Syed, Jana
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 01.12.1995
Elsevier
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Physical Sciences
Science & Technology
CYANOHYDRINS
ANTIBIOTICS
VANCOMYCIN
ACIDS
2-AMINOALCOHOLS
ESTERS
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Summary:Vinyl substituted (1 R,2 S)-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 (1 R,2 S)-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°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. Vinyl-substituted (1 R,2 S)-2-Amino Alcohols derived from ( R)-Cyanohydrins via Grignard Addition were ozonized to (1 R,2 S)-2-Amino-1,3-diols 7
ISSN:0957-4166
1362-511X
DOI:10.1016/0957-4166(95)00390-8