Merging Enantioselective Lewis Base Organocatalysis and Gold(I) Catalysis: A One-Pot Access to Chiral-Fused Polycyclic Compounds

Abstract

Reported herein is a route to functionalized chiral heteroaromatic polycyclic compounds leveraging two unfriendly catalytic cycles in a one-pot sequential process. α-Heteroaromatic-γ-butyrolactones were engaged in a highly regio-, diastereo-, and enantio-selective Lewis base asymmetric allylic alkylation (AAA) with alkyne-functionalized Morita–Baylis–Hillman (MBH) carbonates. Gratefully, due to the low Lewis base catalyst loading, subsequent gold-catalyzed Friedel–Crafts type cyclization, entailing the formation of fused polycyclic compounds, proceeded efficiently, affording structurally complex, highly enantioenriched products.