Generation of reactive alpha-oxo gold carbene intermediates via gold-catalyzed oxidation of allcynes has become an increasing versatile strategy of replacing hazardous diazo carbonyl compounds with benign and readily available: alkynes in the development of efficient synthetic methods: However, one Of the hallmarks of metal carbene/carbenoid chemistry, i.e., insertion into an unactivated c(sp(3))-H bond, has not be realized. This study reveals for the first time that this highly valuable transformation can be readily realized intramolecularly by oxidatively generated beta-diketone-alpha-gold carbenes Using ynones as substrate's. Substrate conformation control via the Thorpe-Ingold effect is the key design feature that enables generally good to excellent efficiencies, and synthetically versatile cyclopentanones including spiro-, bridged; and fused bicyclic ones can be readily accessed.