Synthesis, Enantioselective Separation, and Identification of Racemic Tetralin, Indan, and Benzosuberan Derivatives

Forty chiral substituted tetralins, indans, and benzosuberans were synthesized and resolved by gas chromatography using a chiral stationary phase. The substituent groups include hydroxy, keto, methyl, and methoxy moieties. These types of compounds are known to be biological markers in fossil fuels as well as important intermediates in organic synthesis. Total ion current mass spectrometry was used to detect and identify the separated analytes. Two different derivatized cyclodextrin chiral stationary phases (having somewhat different enantioselectivities) were used. The ring size of the analyte appears to affect enantioresolution. The MS relative ion abundance and/or fragmentation patterns can be used to distinguish between enantiomeric and diastereomeric analytes.