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Paper | Special issue | Vol 99, No. 2, 2019, pp.1170-1182
Published online, 8th January, 2019
DOI: 10.3987/COM-18-S(F)89
Further Studies on the Gold-Catalyzed Oxidative Domino Cyclization/Cycloaddition to Give Polyfunctional Tetracycles

Tobias Groß, Korany A. Ali, Anne Jäger, and Peter Metz*

*Faculty of Chemistry and Food Chemistry, Organic Chemistry I, Technische Universität Dresden, Bergstraße 66, 01069 Dresden, Germany

Abstract

Enyne aldehydes and ketones with ester and ether functions in the tether between the reactive functional groups were subjected to a gold(III)-catalyzed domino process in the presence of a pyridine N-oxide as external oxygen donor. The resulting tetracyclic ketoethers were formed in high yields under mild conditions and with excellent induced diastereoselectivity for substrates featuring a stereogenic center within the enyne tether.