Stereoselective access to the versatile 4-aminohex-5-ene-1,2,3-triol pattern.
We developed a stereocontrolled route allowing potential access to the eight isomers of 4-benzylaminohex-5-ene-1,2,3-triol in two or four steps and ca. 50% yield from readily available chiral nonracemic cis- or trans-alpha,beta-epoxyimine precursors. A new (NH(4))(2)CO(3)-based carboxylation/intramolecular cyclization sequence allowed regio- and stereocontrolled C-3 epoxide opening while neat C-2 hydrolysis was ensured by simple aqueous acidic treatment.
Ayad
Tahar
T
Laboratoire Synthèse et Physicochimie des Molécules d'Intéret Biologique, UMR 5068 CNRS, Université Paul Sabatier, 118 route de Narbonne, 31062 Toulouse Cedex 04, France.
Faugeroux
Vanessa
V
Génisson
Yves
Y
André
Chantal
C
Baltas
Michel
M
Gorrichon
Liliane
L
D003500:Cyclization; D004852:Epoxy Compounds / Q000138:chemical synthesis / Q000737:chemistry; D000441:Hexanols / Q000138:chemical synthesis*; D006868:Hydrolysis; D008968:Molecular Conformation; D013237:Stereoisomerism
C496041:4-aminohex-5-ene-1,2,3-triol; D004852:Epoxy Compounds; D000441:Hexanols