Previously we reported the preparation of diazabicyclic twisted amides based on the bicyclo[3.3.1]nonane and bicyclo[4.3.1]decane scaffolds. Our synthesis employed reductive amination of 3-ketoazacycles with α-and βaminoesters to convergently prepare precursors for Bu 2 SnOmediated lactamisation. Although successful, this approach limited exploration e.g. of alternative ring-sizes and substitution patterns. We describe herein a complementary and more general approach, based upon coupling of key building blocks through photoredox-mediated hydroamination of readily-available enecarbamates 5 (Scheme 1, panel b). Cyclisation either through lactamisation or Buchwald-Hartwig amination gives a broad range of bicyclic twisted amides 6 and anilines 7 wherein the impact of subtle changes in structure upon properties can be probed. for the photoredox-catalysed hydroamination of enecarbamates (Scheme 1). Hence, coupling of substrates 5a-e (prepared from the corresponding saturated amines through electrochemical oxidation and elimination ) with aminoesters 8a-c proceeded in generally good yield (see Supporting Information for full details). Protection of the resulting secondary amines variously as carbamates (P = Cbz, POC) or sulfonamides (P = Ts) enabled the preparation of a library of cyclisation precursors 9a-l. Conversion to the desired diazabicyclic scaffolds was effected by basic ester hydrolysis, removal of the Boc protecting group from the azacycle under acidic conditions, and finally cyclisation using Bu 2 SnO. Attempts to form the [3.2.1]diazabicyclic products 6a,b derived from hydroamination of dihydropyrroles 5a,b with ethyl glycinate 8a failed at the cyclisation step, presumably owing to the high degree of strain in the products: we are unaware of any successful approaches to twisted amides with the [3.2.1]-bicyclic skeleton via amide bond formation. However, we were delighted to find that the use of ethyl aminopropionate 8b as the hydroamination partner led successfully to the formation of the diazabicyclo[4.2.1]nonanes 6c-e in moderate yield. Most notably, the formation of the unprecedented tricyclic system 6e, which contains a fully-substituted carbon, could not have been achieved through our previous reductive amination approach.