219953-62-5Relevant academic research and scientific papers
Stereocontrolled approaches to (+)- and (-)-γ-trifluoromethyl-GABOB, a new hydroxymethylene (statine) dipeptide isostere
Bravo, Pierfrancesco,Corradi, Eleonora,Pesenti, Cristina,Vergani, Barbara,Viani, Fiorenza,Volonterio, Alessandro,Zanda, Matteo
, p. 3731 - 3735 (2007/10/03)
Two efficient approaches to both enantiomers of syn-γ-trifluoromethyl γ-amino β-hydroxy butyric acid (γ-Tfm-GABOB) (10), a new hydroxymethylene (statine) dipeptide isostere, are described. One exploits the recently disclosed 'non-oxidative' Pummerer reaction, by means of which α-lithium alkyl sulfoxides are used as chiral α-hydroxyalkyl anion equivalents in the synthesis of β-amino alcohols. Trifluoropyruvaldehyde-N,S-ketal (R)-11, a novel stereochemically stable synthetic equivalent of α-amino trifluoropropanal, is used in the second approach.
