A practical RhIII-catalyzed cascade olefination/annulation of picolinamides leading to pyrrolo[3,4-b]pyridines has been developed. The reaction shows wide scope, complete regiocontrol and excellent stereoselectivityWe thank Spanish Government (MINECO, CTQ2012-35790) and Madrid regional government (AVANCAT, S2009/PPQ-1634) for financial support. N.R. thanks the MICINN for a Ramón y Cajal contract and the Marie Curie Foundation (CIG: CHAAS- 304085