Dearomatization-bis-alkylation of aromatic and heteroaromatic diesters promoted by Me3SnLi via a stanna-Brook rearrangement.

Reaction of Me3SnLi with aromatic and heteroaromatic diesters proceeds through a fast stanna-Brook rearrangement that generates an stable bis-enolate which can be regioselectively alkylated and cyclized, in one step, to bicyclic compounds containing 6,5-, 6,6-, and 6,7-fused ring systems.