Unsaturated nine-membered ring lactams that contain (E)-olefins within the ring are characterized by planar chiral properties. Thus, selective conversions of the double bond allowed a complete transfer of the planar chiral information into new stereogenic centers The basis of the transformations was the high activation barrier that prevented efficient flipping of the double bond at room temperature (epimerization pR <=> pS) with respect to the ring. Cycloadditions led diastereoselectively to cyclopropano, epimino, epoxy, and dihydroxy azonanones under mild conditions with moderately high yields. The epoxy azonanones were subjected to regio- and diastereoselective transannular epoxide opening/ring contraction sequences to give hydroxy indolizidinones. The regiochemical and stereochemical outcome strongly depends on the configuration of the oxirane and the chiral information of the lactam unit. The so-formed optically active bicycles with defined substitution patterns should serve as versatile building blocks in alkaloid synthesis.