Reactions of lithiated (E)-3-halo-1-phenylsulfonylprop-1-enes and (Z)-1-halo-3-phenylsulfonylprop-1-enes with aldehydes.
(E)-3-Chloro-1-phenylsulfonylprop-1-ene and its iodo- and bromo-analogues, (Z)-1-iodo-3-phenylsulfonylprop-1-ene and (Z)-1-bromo-3-phenylsulfonylprop-1-ene, have each been successfully converted into lithiated carbanions which react regioselectively with aromatic aldehydes to give gamma-alkylated products whose nature depends upon the halogen substituent: the chloro-sulfones yield (2Z)-1-aryl-2-chloro-4-phenylsulfonylbut-2-en-1-ols but the bromo- and iodo-derivatives behave differently, yielding (1E)-trans-4-aryl-3,4-epoxy-1-phenylsulfonylbut-1-enes. In sharp contrast, the same lithiated sulfones react with aliphatic aldehydes to give anti-configured beta-hydroxysulfones which are formed via diastereoselective alpha-alkylation reactions.
Gallagher
Eva T
ET
Centre for Synthesis and Chemical Biology, Department of Chemistry, Trinity College, Dublin 2, Ireland.
Grayson
David H
DH