MiPNO, a new chiral cyclic nitrone for enantioselective amino acid synthesis: the cycloaddition approach.
The resolution of chiral nitrones via derivatization of hydroxylamines was applied to MiPNO, a new, stable, easily prepared chiral cyclic nitrone. The application of MiPNO in totally regio- and diastereo-selective 1,3-dipolar cycloaddition reactions provides an expeditious enantioselective access to unusual gamma-hydroxy alpha-amino acids.
Thiverny
Maryse
M
Département de Chimie Moléculaire, UMR-5250, ICMG FR-2607, CNRS, Université Joseph Fourier, BP-53, 38041, Grenoble, Cedex 9, France.
Philouze
Christian
C
Chavant
Pierre Yves
PY
Blandin
Véronique
V
D000596:Amino Acids / Q000138:chemical synthesis*; D002384:Catalysis; D018360:Crystallography, X-Ray; D003497:Cyclic N-Oxides / Q000737:chemistry*; D003500:Cyclization; D015394:Molecular Structure; D009589:Nitrogen Oxides / Q000737:chemistry*; D013237:Stereoisomerism
C549022:(rac)-2-isopropyl-2,3-dimethyl-1-oxy-2,3-dihydro-imidazol-4-one; D000596:Amino Acids; D003497:Cyclic N-Oxides; D009589:Nitrogen Oxides; C015388:nitrones