Abstract Samarium diiodide promoted the intramolecular reductive couplings of N-alkylated indole and pyrrole derivatives 9–12 and 14 to afford products 15–19 that incorporate seven- and eight-membered rings. They were obtained in good yields and generally with excellent diastereoselectivities. Up to four contiguous stereogenic centres are controlled in this transformation, which is explained by a highly ordered transition structure with the ...