Stereochemistry of palladium-catalyzed asymmetric transformation of chiral 2-alkynyl sulfinates into allenyl sulfones

Article abstract of DOI:10.1246/cl.1998.553

Optically active 2-alkynyl p-toluenesulfinates, possessing chiralily on both the α-carbons of the 2-alkynyl groups and the sulfur atoms of the sulfinates, were readily transformed into chiral allenyl sulfones with high stereospecificity in good yields by treatment with palladium acetate. The stereochemistry of the transformation was determined and the plausible mechanistic pathway is proposed.