Oxygen- and nitrogen-based heterocycles can be rapidly constructed by condensation reactions relying on σ C(sp3)-O bond activation, or cycloisomerization reactions triggered by CC π-bond activation. These σ- and π-activations can be achieved in the presence of a catalytic amount of the calcium ions [Ca(NTf2)]+, which confer high levels of chemo-, regio-, and stereoselectivity. This presentation will summarize our findings in the development of novel synthetic methodologies towards heterocycles using simple calcium salts. Mechanistic considerations based on DFT computations will also be presented.

Catalytic use of a calcium-based Lewis acid for the synthesis of heterocyclic compounds

255th National Meeting (2018)

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