Modular synthesis of bicyclic twisted amides and anilines

Bridged amides and anilines display interesting properties owing to perturbation of conjugation of the nitrogen lone-pair with the adjacent π-system. A convergent approach to diazabicyclic scaffolds which contain either twisted amides or anilines is described, based on the photocatalysed hydroamination of cyclic enecarbamates and subsequent cyclisation. The modular nature of the synthesis allows for variation of the degree of 'twist' and hence the properties of the amides and anilines. A modular approach to the synthesis of twisted bicyclic amides and anilines allows for variation in the degree of overlap between the nitrogen lone pair and the relevant π-system, and hence the structural and physical properties of the products.