Complete ligand-control over newly formed centres can also be observed in much more complex starting materialsfor example, either 1,5-diastereomer (59 and 60) can be generated from an allylic diene derived from (-)-perillaldehyde. The exquisite regio-and chemoselectivity observed deserves comment, as the polyene in which the overall SN2'-like pathway is observed could have given the linear product or undergone an SN2''-like process to add to the olefin in the ring. The higher yield for 60 (68 vs 85%) is likely due a matched/mismatched effect between the substrate's preexisting stereochemistry and the ligand because, although the stereogenic centres are separated by 5 carbons, the 6-membered ring significantly effects the overall shape of the starting material.