Nitrogen-containing heterocycles are important motifs found in a variety of biologically active natural products and pharmaceuticals such as atorvastatin and nakadomarin A. Owing to the abundance of these structures, we envisaged that the combination of a nitro-Mannich reaction and a hydroamination reaction would result in a versatile methodology allowing access to an array of nitrogen-containing heterocycles.The use of a nitrobutyne substrate in combination with a protected imine (Figure 1), enabled efficient access to a selection of disubstituted pyrroles after an isomerization/nitro group elimination sequence. In total, 17 pyrroles were prepared with yields ranging from 21-86%. Further development of this methodology to the enantioselective synthesis of tetrahydropyridine scaffolds has also been established using bifunctional organocatalysis and gold catalysis. In this case the contiguous stereocentres are retained as there is no nitro group elimination. In total, 14 tetrahydropyridines were prepared in good yields (31-72%) and high enantioselectivites (86-96%).

Nitro-Mannich/hydroamination cascades: Versatile access to <i>N</i>-heterocycles using gold catalysis

244th National Meeting (2012)

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Nitro-Mannich/hydroamination cascades: Versatile access to N-heterocycles using gold catalysis