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Stereochemical assignment of the two diastereomeric 4-tert-butyl-7,11-bisarylspiro[5.5]undecane-1,9-diones using two-dimensional nuclear magnetic resonance spectroscopy

✍ Scribed by Dinesh H. Rele; Hari H. Mathur; Girish K. Trivedi; K. V. R. Chary


Publisher
John Wiley and Sons
Year
1986
Tongue
English
Weight
591 KB
Volume
24
Category
Article
ISSN
0749-1581

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✦ Synopsis


Phase-transfer catalysed condensation between 4-ferf-butylcyclohexanone and bis(benza1)acetone yielded two 4-ferf-butyl-7,11-bisarylspiro[5.5]undecane-1,9-dione diastereomers. The stereochemical assignment of these molecules was carried out using two-dimensional (2D) NMR spectroscopy. Combined use of COSY and NOESY spectra of these diastereomers helped in unambiguous and complete proton spin system assignment. In addition, from the application of 2D J-resolved spectra together with the Karplus equation, the exact conformation of the molecules could be established.