174309-35-4Relevant academic research and scientific papers
Stereoselective Synthesis of (1R,2S)-2-Amino-1,3-diols from (R)-Cyanohydrins
Effenberger, Franz,Gutterer, Beate,Syed, Jana
, p. 2933 - 2944 (2007/10/03)
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.
A convenient asymmetric synthesis of anti-β-amino alcohols: An X-ray crystallographic study of (4R)-2,2-dimethyl-4-[(2S)-(diphenylmethyleneamino)-(1S)- hydroxy-3-buten-1-yl]-1,3-dioxolane
Barrett,Seefeld,Williams
, p. 1053 - 1054 (2007/10/02)
anti-β-Diphenylmethyleneamino alcohols have been produced with high relative and absolute stereocontrol in a one-pot process; subsequent deprotection gave anti-β-hydroxy amines in good yield.
