Diastereoselective synthesis and 1H and 13C NMR study of 4-acetyl-2,6-diaroyl-3,5-diaryl-4-ethoxycarbonylthiane-1,1-dioxides

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 1H, 13C and 2D NMR spectroscopic techniques such as H,H-COSY, C,H-COSY and NOESY. Copyright © 2001 John Wiley & Sons, Ltd.