title: An enantiomerically pure 1,5,7-trimethyl-3-azabicyclo[3.3.1]nonan- 2-one as 1H NMR shift reagent for the ee determination of chiral lactams, quinolones, and oxazolidinones.
abstract: The chiral lactam 1 (or its enantiomer ent-1) was shown to be an effective (1)H NMR shift reagent for the ee determination of chiral lactams, quinolones, and oxazolidinones. It was successfully employed in many cases in which a detection of enantiomers by chromatographic methods failed. The method was extended to a broader range of simple substrates bearing a lactam moiety to evaluate its scope. The NH signals of the substrate enantiomers showed the strongest separation and were used for (1)H NMR integration. In most cases, compound 1 (1.5 equiv; 0.06 M solution) induced a baseline separation of the NH signals and it can consequently be regarded as a generally applicable shift reagent for chiral products with a lactam moiety.
authors.affiliation: Philipps-Universität Marburg, Fachbereich Chemie, D-35032 Marburg, Germany. thorsten.bach@ch.tum.de
authors.forename: Hermann
authors.initials: H
authors.lastname: Bergmann
authors.forename: Benjamin
authors.initials: B
authors.lastname: Grosch
authors.forename: Stephanie
authors.initials: S
authors.lastname: Sitterberg
authors.forename: Thorsten
authors.initials: T
authors.lastname: Bach