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Diastereoselective synthesis and 1 H and 13 C NMR study of 4‐acetyl‐2,6‐diaroyl‐3,5‐diaryl‐4‐ethoxycarbonylthiane‐1,1‐dioxides
Author(s) -
Renuga S.,
Selvaraj S.,
Perumal S.,
Lycka A.,
Gnanadeebam M.
Publication year - 2001
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.897
Subject(s) - chemistry , diastereomer , two dimensional nuclear magnetic resonance spectroscopy , conjugate , ethyl acetoacetate , stereochemistry , proton nmr , nuclear overhauser effect , nuclear magnetic resonance spectroscopy , organic chemistry , catalysis , mathematical analysis , mathematics
Conjugate addition of ethyl acetoacetate to 2,2′‐sulfonylbis(1,3‐diarylprop‐2‐en‐1‐ones) afforded a diastereom‐eric mixture (in a ratio of ∼65:35) of 4‐acetyl‐2,6‐diaroyl‐3,5‐diaryl‐4‐ethoxycarbonylthiane‐1,1‐dioxides differing in configuration at C‐4. The stereochemistry of the diastereomeric thianes was established by 1 H , 13 C and 2D NMR spectroscopic techniques such as H,H‐COSY, C,H‐COSY and NOESY. Copyright © 2001 John Wiley & Sons, Ltd.