4.8 Review

Construction of Medium-Sized Rings by Gold Catalysis

Journal

CHEMICAL REVIEWS
Volume 121, Issue 14, Pages 8926-8947

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.chemrev.0c00793

Keywords

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Funding

  1. JSPS KAKENHI [JP18H03906, JP20K15269, JP17H04877, JP20H04793]

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This review focuses on methodologies for constructing medium-sized rings using gold catalysis, particularly emphasizing the pathway, precursor selection, catalyst choice, and mechanistic attributes. Gold-mediated cyclization reactions show significant potential in building 7-membered rings and medium-sized (8-11-membered) ring structures.
Compounds having cyclic molecular frameworks are highly regarded for their abundance and diverse utilities. In particular, medium-sized carbocycles and heterocycles exist in a broad spectrum of natural products, bioactive therapeutics, and medicinally significant synthetic molecules. Metal-mediated methods have been developed for the preparation of compounds containing a medium-sized ring (MSR) through cyclization of different classes of substrates and acyclic precursors. This review focuses on the methodologies for construction of MSRs via gold catalysis. Given the challenges in enabling the assembly of different ring sizes, we present here accounts on Au-mediated cyclization giving notable 7-membered and medium-sized (8-11-membered ring) structures. Emphasis on the pathway and mode of cyclization and the selection of precursors ranging from structurally biased compounds were outlined. Reactivity patterns and the choice of efficient Au catalysts for controlling reaction performance and selectivity in addition to mechanistic attributes are examined.

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