- Diastereoselective synthesis of substituted 2-Amino-1,3-propanediols from morita Baylis-Hillman adducts
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We report herein a new diastereoselective approach to substituted 2-amino-1,3-propanediols with anti relative stereochemistry from Morita-Baylis-Hillman (MBH) adducts. These structural moieties have been used as intermediates for the synthesis of several
- Paioti, Paulo H. S.,Rezende, Patri?cia,Coelho, Fernando
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experimental part
p. 285 - 293
(2012/05/05)
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- Stereoselective Synthesis of (1R,2S)-2-Amino-1,3-diols from (R)-Cyanohydrins
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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.
- Effenberger, Franz,Gutterer, Beate,Syed, Jana
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p. 2933 - 2944
(2007/10/03)
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