Enantioselective Palladium-Catalyzed N-Allylation of Lactams

N-Deprotonated five-, six-, seven, and nine-membered lactams undergo smooth palladium-catalyzed N-allylation with methyl-(pent-3-en-2-yl)-carbonate or 2-chloro-3-pentene. With axially chiral bisphosphane ligands, enantioselectivities ranging from 83 to 97% ee are reached. The configuration of one of the allylation products is assigned unambiguously by the preparation of a relay compound and by analogy to the others. Using the enantioselective allylation protocol as a key step, delta-valerolactam is converted into (4S,9aR)-4-methylquinolizidine.