REGIOSELECTIVE CONJUGATE ADDITION OF SULFONYLALLYL CARBANIONS TO α,β-UNSATURATED KETONES

Article abstract of DOI:10.1016/S0040-4039(01)90474-5

Ambident lithium carbanions of allyl phenyl sulfones add 1,4-α to both acyclic and cyclic enones exclusively if HMPA is present in the medium; in contrast, 1,2-α addition to cyclic enone is the major kinetic course in the absence of HMPA, which is followed by rearrangement to the 1,4-γ adduct.