(1-Naphthyl)(trifluoromethyl) O-carboxy anhydride as a chiral derivatizing agent: eclipsed conformation enforced by hydrogen bonding.
The preparation of the (1-naphthyl)(trifluoromethyl) O-carboxy-anhydride 1 and its use as a chiral derivatizing agent with several alpha-chiral primary amines are reported. The very large Delta delta(RS) values observed in (1)H NMR have been correlated with a marked preference of the corresponding alpha-hydroxy-amides for the eclipsed conformation. In comparison, the related O-methylated amides are shown to adopt staggered conformations, which substantiates the critical role of intramolecular hydrogen bonding in maximizing the anisotropic effect.
Thillaye du Boullay
Olivier
O
Laboratoire Hétérochimie Fondamentale et Appliquée du CNRS (UMR 5069) Université Paul Sabatier, 118, route de Narbonne, 31062 Toulouse Cedex 09, France.
Alba
Aurélie
A
Oukhatar
Fatima
F
Martin-Vaca
Blanca
B
Bourissou
Didier
D
D001596:Benzylamines / Q000737:chemistry; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*; D013237:Stereoisomerism
C533380:(1-naphthyl)(trifluoromethyl) O-carboxy anhydride; D001596:Benzylamines; D009281:Naphthalenes; C030796:benzylamine