Enantioselective synthesis of a-hydroxy-ß-amino acids from a-amino acids mediated by sulfoxides
Por:
Sánchez-Obregón R., Salgado F., Ortiz B., Díaz E., Yuste F., Walls F., García Ruano J.L.
Publicada:
1 ene 2007
Resumen:
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 ?-amino sulfoxides into ?-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. © 2007 Elsevier Ltd. All rights reserved.
Filiaciones:
Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Coyoacan 04510, México D. F., Mexico
Departamento de Química Orgánica (C-I), Facultad de Ciencias, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain
|