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Abstract
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.
Content
Supplementary material
Supplementary Information: Modular Synthesis of Bicyclic Twisted Amides and Anilines
Experimental procedures, compound characterisation data (NMR, IR, MS, X-ray crystallography), determination of non-aqueous pKas, computational studies of structure and pKa, experimental NMR spectra.
