Racematspaltung und Bestimmung der absoluten Konfiguration von 2, 6‐disubstituierten Bicyclo [3.3.1]nonanen

Resolution and Determination of the Absolute Configuration of 2,6‐Disubstituted Bicyclo[3.3.1]nonanes (±)‐ endo, endo ‐Bicyclo [3.3.1]nonane‐2,6‐diol was resolved via diastereomeric camphanic acid esters. Conversion of the (+)‐enantiomer 2 via (+)‐ 5 and (+)‐ 6 as key intermediates gave (+) methyl 3‐(3‐oxocyclohexyl)‐propionate ( 7 ) which independently could be prepared also from the known (+)‐( R )‐3‐oxo‐cyclohexane‐carboxylic acid ( 8 ). These chemical correlations establish the absolute configuration of (+) ‐2 , (+) ‐5 and (+) ‐6 as well as that of (+)‐bicyclo [3.3.1]nonane‐2,6‐dione ( 1 ) obtained by oxidation of (+) ‐2 . The chiroptical properties of 1 and 6 are discussed.