Abstract:
The synthesis of the optically pure (2S, 3S)- and (2R, 3S)-3-amino-2-hydroxybutanoic acids from commercially available ( S)alanine derivatives is reported. The key step of the synthetic sequence is the conversion of gamma-amino sulfoxides into gamma-amino alcohols by treatment with TFAA and sym-collidine. The efficiency of this non-oxidative Pummerer reaction (NOPR) is dependent on the stereochemistry of the starting sulfoxide. (c) 2007 Elsevier Ltd. All rights reserved.