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

✍ Scribed by Hans Gerlach

Publisher
John Wiley and Sons
Year
1978
Tongue
German
Weight
299 KB
Volume
61
Category
Article
ISSN
0018-019X

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✦ Synopsis

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.

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