Tetrahedron Asymmetry p. 3731 - 3735 (1998)
Update date:2022-09-26
Topics:
Bravo, Pierfrancesco
Corradi, Eleonora
Pesenti, Cristina
Vergani, Barbara
Viani, Fiorenza
Volonterio, Alessandro
Zanda, Matteo
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.
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Doi:10.1021/ja983153j
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(1972)