Abstract:
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The design and development of 5,5’-bistriazoles featuring aminomethyl substituents is discussed. An efficient synthetic
procedure for the selective preparation of 4,4’-bis(aminomethyl)-5,5’-bistriazoles from commercially available
propargylamine derivatives and benzyl azide has been optimized. The first experimental determination of the
configurational stability of 5,5’-bistriazoles is disclosed on the basis of rotational energy barriers and half-life times. Fast
racemization was observed for a bistriazole possessing solely axial chirality whereas a more heavily substituted bistriazole
involving axial and central chirality proved to be configurationally stable. A successful catalytic application has been
implemented by using a N,N-dimethylpropargylamine-derived 5,5’-bistriazole as a multidentate ligand controlling the
product selectivity (single vs. double addition) in scandium(III)-catalyzed nucleophilic additions of indoles to isatin
electrophiles. |