Cycloisomerization of π-Coupled Heteroatom Nucleophiles by Gold Catalysis: En Route to Regiochemically defined Heterocycles

Since the dawn of millennium, catalytic gold chemistry is at the forefront to set off diverse organic reactions via unique activation of pi-bonded molecules. Within this purview, cycloisomerization of heteroatom nucleophiles linked to a pi-system is one of the well recognized chemistry for the construction of numerous heterocyclic cores. Though the rudimentary aspects of this transformation are reviewed by several groups in different timeline, a holistic view on regiochemistry of such reactions went largely overlooked. Hence, this account emphasizes the gold catalyzed regioselective cycloisomerization of structurally distinctive pi-connected hetero-nucleophiles leading to different heterocycles documented in the last two decades. From an application perspective, this account also highlights those methodologies which find a role in the total synthesis of natural products. Wherever appropriate, mechanistic details and contributing factors for selectivity are also discussed.

Automated summary

This article focuses on the regioselective cycloisomerization of structurally distinctive pi-connected hetero-nucleophiles catalyzed by gold, leading to the construction of different heterocycles. It also discusses the application of these methodologies in the total synthesis of natural products, along with the contributing factors for selectivity.