(2E)-N-(2-Iodo-4,6-dimethylphenyl)-2-methylbut-2-enamide

The title compound, C14H18INO, crystallizes as +sc/+sp/+sc 2-iodoanilide molecules (and racemic opposites) and shows significant intermolecular I center dot center dot center dot O interactions in the solid state, forming dimeric pairs about centres of symmetry. Under asymmetric Heck conditions, the S enantiomer of the dihydroindol-2-one was obtained using (R)-(+)-2,2'- bis(diphenylphosphino)1,1'-binaphthyl [(R)-BINAP], suggesting a mechanism that proceeds by oxidative addition to give the title (P) enantiomer of the compound and pro-S coordination of the Re face of the alkene in a conformation similar to that defined crystallographically, except that rotation about the C-C bond of the butenyl group is required.