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

Hermann Bergmann, Benjamin Grosch, Stephanie Sitterberg, Thorsten Bach

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Abstract

The chiral lactam 1 (or its enantiomer ent-1) was shown to be an effective 1H 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 1H 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.

Original languageEnglish
Pages (from-to)970-973
Number of pages4
JournalJournal of Organic Chemistry
Volume69
Issue number3
DOIs
StatePublished - 6 Feb 2004

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