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. 2023 Oct;88(10):e202300314.
doi: 10.1002/cplu.202300314. Epub 2023 Aug 21.

Gold-Catalyzed Asymmetric Transformation of Hydroxylated Propargylic Esters

Carlos D Quintanilla  1 , Ke Zhao  1 , Liming Zhang  1
Affiliations

Gold-Catalyzed Asymmetric Transformation of Hydroxylated Propargylic Esters

Carlos D Quintanilla et al. Chempluschem. 2023 Oct.

Abstract

By combining tandem asymmetric gold catalysis and subsequent stereoconvergent hydrolysis of enol ester in a one-pot process, hydroxylated propargylic esters are converted into chiral β-oxygenated ketones with mostly good enantiomeric ratios and in largely good to excellent yields. The product chiral center is formed via stereoselective cyclization of a hydroxylated allenyl ester intermediate, which is enabled by asymmetric gold-ligand cooperation.

Keywords: catalysis; chiral; gold; ligand; metal-ligand cooperation.

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Conflict of interest statement

Conflict of Interests

The authors declare no conflict of interest.

Figures

Scheme 1.
Scheme 1.
Gold-catalyzed asymmetric allenol cyclization achieved via metal-ligand cooperation: a previous study and this work.
See this image and copyright information in PMC

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