1,3-Bis(trimethylsilyl)propyl phenyl sulfone undergoes, in contrast
to all reported sulfones bearing α-hydrogen atoms, an initial ortho metalation to an aryllithium at
low temperature, which transmetalates quantitatively to the corresponding α-sulfonyl
organolithium intermediate. Both organolithiums react selectively
with aldehydes to give the corresponding products in good to excellent yields
with high selectivity.
carbanions - transmetalation - silanes - sulfones - Julia olefination