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.

The (1-naphthyl)(trifluoromethyl) O-carboxy anhydride effectively induces the eclipsed conformation in alpha-chiral primary amines, highlighting the importance of intramolecular hydrogen bonding for maximizing anisotropic effect.

Paper

(1-Naphthyl)(trifluoromethyl) O-carboxy anhydride as a chiral derivatizing agent: eclipsed conformation enforced by hydrogen bonding.

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