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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
Author(s) -
Rele Dinesh H.,
Mathur Hari H.,
Trivedi Girish K.,
Chary K. V. R.
Publication year - 1986
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.1260240812
Subject(s) - chemistry , diastereomer , undecane , two dimensional nuclear magnetic resonance spectroscopy , spectroscopy , molecule , nuclear magnetic resonance spectroscopy , nuclear overhauser effect , stereochemistry , spectral line , condensation , proton nmr , crystallography , organic chemistry , physics , quantum mechanics , astronomy , thermodynamics
Phase‐transfer catalysed condensation between 4‐ tert ‐butylcyclohexanone and bis(benzal)acetone yielded two 4‐ tert ‐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.