TRANSFER OF ASSYMETRY BY THE PALLADIUM-CATALYZED ALKYLATION OF CHIRAL ALLYLIC SULFINATES

Article abstract of DOI:10.1246/cl.1984.929

The pallladium-catalyzed substitution of chiral allylic sulfinates was performed by the initial transformation of the sulfinates into allyl sulfones and the subsequent alkylation of the sulfones with retention of configuration.Reaction of trans- and cis-2-butenyl (S)-(-)-p-toluenesulfinate with the sodium salt of dimethyl malonate was undertaken in the presence of tetrakis(triphenylphosphine)palladium and triphenylphosphine to produce dimethyl (S)-(+)- and (R)-(-)-1-buten-3-ylmalonate, respectively, with the α-alkylated product, dimethyl 2-butenylmalonate.