Regioselective and Stereoselective Diels-Alder reactions of Unsymmetrical 1,2-Disubstituted Vinyl Sulfones with a Monovinylporphyrin
Yon-Hin, P., Wijesekera, T.P., and David Dolphin
New J. Chem.
A study of the Diels-Alder reactions of several 1,2-disubstituted vinyl sulfones with a β-methyl-β'-monovinylporphyrin (I) shows that the cycloadditions are highly regioselective and that stereochemical control can be manipulated by replacing a carboxyl ester group by a cyano group or by changing of the dienophile. Thus, reacting I with (E)- and (Z)-PhSO2CH=CHCN gave adducts II and III.