(1-Naphthyl)(trifluoromethyl) O-carboxy anhydride as a chiral derivatizing agent: eclipsed conformation enforced by hydrogen bonding |
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Authors: | Thillaye du Boullay Olivier Alba Aurélie Oukhatar Fatima Martin-Vaca Blanca Bourissou Didier |
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Affiliation: | Laboratoire Hétérochimie Fondamentale et Appliquée du CNRS (UMR 5069) Université Paul Sabatier, 118, route de Narbonne, 31062 Toulouse Cedex 09, France. |
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Abstract: | 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. |
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